NO124726B - - Google Patents

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NO124726B
NO124726B NO69968A NO96869A NO124726B NO 124726 B NO124726 B NO 124726B NO 69968 A NO69968 A NO 69968A NO 96869 A NO96869 A NO 96869A NO 124726 B NO124726 B NO 124726B
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Norway
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ethyl
imino
phenylsulfonyl
imidazolidine
chloride
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NO69968A
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Norwegian (no)
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Henri Dietrich
C Lehmann
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Ciba Geigy Ag
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Publication of NO124726B publication Critical patent/NO124726B/no

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C07D203/24—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Analogifremgangsmåte for fremstilling av farmakologisk aktive, nye derivater av 1-(p-aminoalkyl-fenylsulfonyl)-2-imino-imidazolidin. Analogy process for the preparation of pharmacologically active, new derivatives of 1-(p-aminoalkyl-phenylsulfonyl)-2-imino-imidazolidine.

Nærværende oppfinnelse vedrorer en analogifremgangsmåte for fremstilling av farmakologisk aktive, nye derivater av 1-(p-aminoalkyl-fenylsulfonyl)-2-imino-imidazolidin. The present invention relates to an analogue method for the production of pharmacologically active, new derivatives of 1-(p-aminoalkyl-phenylsulfonyl)-2-imino-imidazolidine.

Forbindelser med den generelle formel I, Compounds of the general formula I,

hvor m er 2 eller 3, where m is 2 or 3,

betyr en alkylgruppe med hoyst 12 karbonatomer, en alkenylgruppe med 3-5 karbonatomer, en cykloalkyl-eller cykloalkenylgruppe med hoyst 7 karbonatomer eller en fenylalkylgruppe med hoyst 9 karbonatomer, 1*2 hydrogen eller en alkylgruppe med hoyst 2 karbonatomer , means an alkyl group with a maximum of 12 carbon atoms, an alkenyl group with 3-5 carbon atoms, a cycloalkyl or cycloalkenyl group with a maximum of 7 carbon atoms or a phenylalkyl group with a maximum of 9 carbon atoms, 1*2 hydrogen or an alkyl group with a maximum of 2 carbon atoms,

hydrogen, en alkylgruppe eller kloralkylgruppe med hoyst 7 karbonatomer, en alkenylgruppe med hoyst 5 karbonatomer, en cykloalkyl- eller cykloalkenylgruppe med hoyst 8 karbonatomer, en fenylgruppe eller en fenyl-alkyl- eller fenylalkenylgruppe med hoyst 10 karbonatomer, idet den som R^ henh. i R^ foreliggende fenylgruppe kan være substituert med halogen inntil atomnummer 35, trifluormetylgrupper, alkylgrupper med hoyst 4 karbonatomer, hydroksylgrupper, alkoksy- eller alkyltiogrupper med hoyst 2 karbonatomer enkelt til tredobbelt, hydrogen, an alkyl group or chloroalkyl group with a maximum of 7 carbon atoms, an alkenyl group with a maximum of 5 carbon atoms, a cycloalkyl or cycloalkenyl group with a maximum of 8 carbon atoms, a phenyl group or a phenyl-alkyl or phenylalkenyl group with a maximum of 10 carbon atoms, as R in R^ the phenyl group present can be substituted with halogen up to atomic number 35, trifluoromethyl groups, alkyl groups with at most 4 carbon atoms, hydroxyl groups, alkoxy or alkylthio groups with at most 2 carbon atoms single to triple,

og R^ hydrogen eller metylgruppen, and R^ hydrogen or the methyl group,

og deres addisjonssalter med uorganiske eller.organiske syrer er hittil ikke kjente. and their addition salts with inorganic or organic acids are not known to date.

Forbindelsene som fremstilles ifolge oppfinnelsen har ved per-oral eller parenteral administrasjon hypoglykemisk virkning, som karakteriserer dem som egnet til behandling av sukkersyk-dommer . The compounds produced according to the invention have a hypoglycaemic effect on per-oral or parenteral administration, which characterizes them as suitable for the treatment of diabetes.

Den hypoglykemiske virkning påvises ved standardforsok på varmblodige dyr, f.eks. på rotter. L\_ter fremgangsmåten ifolge oppfinnelsen fremstiller man forbindelser med den generelle formel I, idet man omsetter et reaksjonsdyktig funksjonelt derivat av en sulfonsyre med den generelle formel II, The hypoglycaemic effect is demonstrated by standard experiments on warm-blooded animals, e.g. on rats. According to the method according to the invention, compounds of the general formula I are prepared, by reacting a reactive functional derivative of a sulfonic acid with the general formula II,

hvor m, R~ og R^ har den under formel I angitte where m, R~ and R^ have the under formula I indicated

betydning, importance,

med en forbindelse med den generelle formel III, with a compound of the general formula III,

hvor og R2 har den under formel I angitte betydning, og overforer eventuelt reaksjonsproduktet med en uorganisk eller organisk syre til et addisjonssa 11. Som reaksjonsdyktig funksjonelt derivat av en sulfonsyre med den generelle formel II egner seg f.eks. et halogenid, spesielt et klorid, eller også et anhydrid med den generelle formel Ila, where and R2 has the meaning given under formula I, and possibly transfers the reaction product with an inorganic or organic acid to an addition sa 11. As a reactive functional derivative of a sulfonic acid with the general formula II, e.g. a halide, especially a chloride, or also an anhydride of the general formula IIa,

hvor m, R^ og R^ har den under formel I angitte betydning. where m, R^ and R^ have the meaning given under formula I.

Omsetningen finner fortrinnsvis sted i nærvær av et med vann blandbart eller ikkeblandbart inert organisk opplosningsmiddel i nær- oller fravær av vann. Egnede inerte organiske opplosningsmidler er f.eks. hydrokarboner, som benzen, toluen eller xylen, eterlignende væsker, som eter, dioksan eller tetrahydrofuran, klorerte hydrokarboner, som metylenklorid, og lavere ketoner, som aceton eller metyletylketon. Det er fordelaktig å tilfore reaksjonsopplosningen et syrebindende middel. Som slike egner seg f.eks. uorganiske baser eller salter, f.eks. alk al ime Lal 1hydroksyder, alkalimetallhydrogenkarbonater, alkati-metal Ikarbona ler eller alk al irne tall fosfater , som de tilsvarende natrium- eller kaliumforbindelser. Videre lar seg også organiske baser, som f.eks. pyridin, trimetyl- eller trietylamin, N,N-diLsopropyl-etylamin eiLer colLidin, anvende, hvilke, tilsatt i overskudd, også kan anvendes sorn oppldsningsmiddel. The reaction preferably takes place in the presence of a water-miscible or immiscible inert organic solvent in the presence or absence of water. Suitable inert organic solvents are e.g. hydrocarbons, such as benzene, toluene or xylene, ether-like liquids, such as ether, dioxane or tetrahydrofuran, chlorinated hydrocarbons, such as methylene chloride, and lower ketones, such as acetone or methyl ethyl ketone. It is advantageous to add an acid-binding agent to the reaction solution. As such, e.g. inorganic bases or salts, e.g. alkali metal hydroxides, alkali metal hydrogen carbonates, alkali metal carbons or alkali metal phosphates, such as the corresponding sodium or potassium compounds. Furthermore, organic bases, such as e.g. pyridine, trimethyl- or triethylamine, N,N-diLsopropyl-ethylamine or collidine, use which, added in excess, can also be used as a solvent.

Utgangss to f f er med den generelle formel II er f.eks. slike forbindelser, hvis symboler rn, R,, og R. stemmer overens med symbolene som er oppregnet i tilknytning til formel I. En gruppe av slike utgangsstoffer, sulfonylklorider, hvis rest R,, er en lavere alkylgruppe, kan f.eks. fremstilles, når man omsetter lavere alifatiske karboksarnider, hvilke ved nitrogenet er substituert med fenetyl- eller med en fenylpropylgruppe, med klorsulfonsyre. Outputs two f f are with the general formula II is e.g. such compounds, whose symbols rn, R,, and R. correspond to the symbols listed in connection with formula I. A group of such starting substances, sulfonyl chlorides, whose residue R,, is a lower alkyl group, can e.g. are produced, when one reacts lower aliphatic carboxarnides, which are substituted at the nitrogen with a phenethyl or with a phenylpropyl group, with chlorosulfonic acid.

For fremstilling av en andre gruppe av sulfonylklorider med den generelle formel II, hvis rest R^ er en eventuelt substituert fenylgruppe, går man f.eks. ut fra eventuelt substituerte ben-zoylklorider, omsetter disse med p-nitro-fenetylamin eller med p-nltro-fenyl-propylaminer til tilsvarende N-(p-nitro-fenetyl)-henh. N-(p-nitro-fenylpropy1)-benzamider. Disse nitroforbin-deiser reduserer man med jernpulver i saltsyre til tilsvarende N-(p-amino-fenetyl)- henh. N-(p-amino-fenylpropyl)-benzamider. Endelig diazoterer man reduksjonsproduktene med natriumnitrit i saltsyre og tilsetter diazoniumsaltopplosningen til en med svoveldioksyd mettet opplbsning av cupriklorid i vann og is-eddrk. For the preparation of a second group of sulfonyl chlorides with the general formula II, whose residue R^ is an optionally substituted phenyl group, one goes, e.g. from optionally substituted benzoyl chlorides, react these with p-nitro-phenethylamine or with p-nitro-phenyl-propylamines to the corresponding N-(p-nitro-phenethyl)-henh. N-(p-nitro-phenylpropyl)-benzamides. These nitrophorbins are reduced with iron powder in hydrochloric acid to the corresponding N-(p-amino-phenethyl)-property. N-(p-amino-phenylpropyl)-benzamides. Finally, the reduction products are diazotized with sodium nitrite in hydrochloric acid and the diazonium salt solution is added to a sulfur dioxide-saturated solution of cupric chloride in water and iced vinegar.

Etter en 'andre-fremgangs-måte fremstilles forbindelser med den gerverelle formel l, idet man omsetter en syre- med den generelle formel IV, hvor R^.har den under formel I angitte betydning, eller et reaksjonsdyktig funksjonelt derivat av en slik syre med en forbindelse med den generelle formel V, According to a second method, compounds with the Gerverel formula I are prepared, by reacting an acid with the general formula IV, where R has the meaning given under formula I, or a reactive functional derivative of such an acid with a compound of the general formula V,

hvor m, , R2 og R^ har den under formel I angitte where m, , R 2 and R 3 have the under formula I indicated

betydning, importance,

og overforer eventuelt den erholdte forbindelse med en uorganisk eller organisk syre til et addisjonssalt. Acyleringen henh. benzoyleringen av forbindelsen V gjennomføres på i og for seg kjent måte, altså f.eks. ved omsetning med tilsvarende syre-halogenider, -anhydrider eller blandede -anhydrider, fortrinnsvis i nærvær av et syrebindende eller vannbindende middel eller ved behandling med reaktive syreeste-re. .Omsetningen finner fortrinnsvis sted i nærvær -av et inert organisk oppldsningsmiddel. Egnede i-nerte organiske opptdsnings-midler er f.eks. hydrokarboner som f.'eks. benzen, toluen eller xylen, eterlignende væsker, som eter, dioksan eller tetrahydrofuran, klorerte hydrokarboner, som rnetylenk lorid, og lavere ketoner, som f.eks. aceton eller metyletylketon. Det er fordelaktig å tilfore reaksjonsopplosningen et syrebindende middel. Som slike egner seg f.eks. uorganiske baser eller salter, f.eks. alkalimetallhydroksyder, alkalimetallhydrogenkarbonater, alkalimetallkarbonater eller alkalimetallfosfater, som de tilsvarende natrium- eller kaliumforbindelser. Videre lar seg også organiske baser, som f.eks. pyridin, trimetyl- eller trietylamin, N,N-diisopropyl-etylamin eller collidin anvende, and optionally transfers the compound obtained with an inorganic or organic acid to an addition salt. The acylation acc. the benzoylation of compound V is carried out in a manner known per se, i.e. e.g. by reaction with corresponding acid halides, anhydrides or mixed anhydrides, preferably in the presence of an acid-binding or water-binding agent or by treatment with reactive acid esters. The reaction preferably takes place in the presence of an inert organic solvent. Suitable inert organic thickeners are e.g. hydrocarbons such as benzene, toluene or xylene, ether-like liquids, such as ether, dioxane or tetrahydrofuran, chlorinated hydrocarbons, such as methylene chloride, and lower ketones, such as e.g. acetone or methyl ethyl ketone. It is advantageous to add an acid-binding agent to the reaction solution. As such, e.g. inorganic bases or salts, e.g. alkali metal hydroxides, alkali metal hydrogen carbonates, alkali metal carbonates or alkali metal phosphates, as the corresponding sodium or potassium compounds. Furthermore, organic bases, such as e.g. pyridine, trimethyl- or triethylamine, N,N-diisopropyl-ethylamine or collidine use,

hvilke, tilsatt, i overskudd, også kan anvendes som opplosningsmiddel. which, added, in excess, can also be used as a solvent.

I utforingen av denne fremgangsmåte omsettes f.eks. en syre med den generelle formel IV med en forbindelse med' den generelle formel V i nærvær av et karbodiimid, som f.eks. dicykloheksyl-karbodiimid, i et inert opplosningsmiddel, som f.eks, tetrahydrofuran. Lavere alkylestere som f.eks. metylesteren eller etylesteren av syrer med den generelle formel IV, gir ved opp-varmning med forbindelser med den generelle formel V de tilsvarende substituerte amider med dea generelle formel I. In carrying out this method, e.g. an acid of the general formula IV with a compound of the general formula V in the presence of a carbodiimide, which e.g. dicyclohexyl carbodiimide, in an inert solvent, such as tetrahydrofuran. Lower alkyl esters such as e.g. the methyl ester or the ethyl ester of acids of the general formula IV, on heating with compounds of the general formula V, gives the corresponding substituted amides of the general formula I.

Som ytterligere utforelsesform av denne fremgangsmåte omsettes f.eks. et halogenid eller anhydrid, spesielt et blandet anhydrid med en karbonsyrehalvester med .en forbindelse med den generelle formel V, fortrinnsvis i nærvær av et syrebindende middel, f.eks- en sterk tertiær organisk base som trietylamin, pyridin eller s-col lidin,. som i overskudd også kan tjene som reaksjons-medium.. As a further embodiment of this method, e.g. a halide or anhydride, especially a mixed anhydride with a carboxylic acid half-ester with a compound of the general formula V, preferably in the presence of an acid-binding agent, e.g. a strong tertiary organic base such as triethylamine, pyridine or s-col lidine. which in excess can also serve as a reaction medium..

Reaksjonsdyktige estere av syrer med den generelle formel IV er f.eks. deres p-nitro-f en.ylester. og cyanmetyl es t ere , som reagerer med forbindelser med derv generelle formel V i inerte organiske opplosningsmldler. Reactive esters of acids with the general formula IV are e.g. their p-nitro-phenyl esters. and cyanomethyl esters, which react with compounds of general formula V in inert organic solvents.

De som utgangsprodukter med den generelle.formel V dnskede forbindelser oppnås ved hydrolyse f.eks. av de under den generelle formel I fallende imid.azolidiner med den generelle formel Ia, Those as starting products with the general formula V desired compounds are obtained by hydrolysis, e.g. of the imidazolidines falling under the general formula I with the general formula Ia,

hvor m, R^, R2 og R^ har den under formel I angitte betydning. Etter en videre fremgangsmåte når man til utgangsstoffene med den generelle formel V, idet man omsetter substituerte p-(amino-alkyl)-benzensulfonamider med den generelle formel VI, where m, R^, R2 and R^ have the meaning given under formula I. Following a further procedure, the starting materials with the general formula V are reached, by reacting substituted p-(amino-alkyl)-benzenesulfonamides with the general formula VI,

hvor symbolene m og R^ har den under formel I angitte where the symbols m and R^ have the one indicated under formula I

betydning, importance,

med substituerte N-(2-bromalkyl)-cyanamider i alkalisk medium [lit.: E. Miller et al. J.am.chem.Soc. 62, 2101 (1940)]. with substituted N-(2-bromoalkyl)-cyanamides in alkaline medium [lit.: E. Miller et al. J. Am. Chem. Soc. 62, 2101 (1940)].

Etter en tredje fremgangsmåte ifolge oppfinnelsen fremstiller man forbindelser med den generelle formel I, Idet man kondenserer forbindelser med den generelle formel VII, According to a third method according to the invention, compounds with the general formula I are prepared, By condensing compounds with the general formula VII,

hvor m, R^, R2, R2 og R^ har den under formel I angitte betydning og where m, R^, R2, R2 and R^ have the meaning given under formula I and

R^ betyr hydrogen, en a-rylmetyl-, diarylmetyl- eller en R 1 means hydrogen, an a-arylmethyl-, diarylmethyl- or a

triarylmetylgruppe, metyl- eller allylgruppen, triarylmethyl group, the methyl or allyl group,

med et reaksjonsdyktig cyansyrederivat under ringslutning og eventuelt under avspaltning av et R^-halogenid og overforer eventuelt den erholdte forbindelse med en uorganisk eller organisk syre til et addis jonssalt. R^ er som arylrnetyl-, diarylmetyl- eller triarylmetylgruppe f.eks. benzyl-, benzhydryl-henh. tritylgruppen. with a reactive cyanic acid derivative during ring closure and optionally during cleavage of an R^ halide and optionally transfers the obtained compound with an inorganic or organic acid to an addition ion salt. R 1 is as arylmethyl, diarylmethyl or triarylmethyl group, e.g. benzyl-, benzhydryl-enh. the trityl group.

Som reaksjonsdyktige cyansyrederivater egner seg halogencyaner, som klorcyan eller bromcyan eller cyansyreestere, spesielt cyansyrefenylester. Omsetningen finner fortrinnsvis sted i nærvær av et med vann blandbart eller ikkeblandbart inert organisk opplosningsmiddel i nær- eller fravær av vann. Egnede inerte organiske opplosningsmidler er f.eks. hydrokarboner, som benzen, toluen eller xylen, lavere alkanoler, som metanol eller etanol, elerlignende væsker, som eter, dioksan eller tetrahydrofuran, klorerte hydrokarboner, som rnetyl enk lorid, lavere ketoner, som aceton eller metyletylketon, karboksylsyreestere, som eddiksyreetylester, karboksylsyrenitriler, som acetonitril eller sulfoner, som tetrahydro-tiofen-1,1-dioksyd. Omsetningen kan foretas i nær- eller fravær av et syrebindende middel. Som syrebindende midler egner seg uorganiske baser eller salter, f.eks. a 1k a timetal1hydroksyder, alkalimetallhydrogenkarbona ter, alka 1 ime taLIkarbonater eller alkalimetall fos fater, som de tilsvarende natrium- eller kaliumforbindelser. Videre kan også kalsiumkarbonater såvel som kalsiumfosfater og magnesiumkarbo-nat anvendes. Halogen cyans, such as cyanochlorine or cyanobromine or cyanic acid esters, especially cyanic acid phenyl ester, are suitable as reactive cyanic acid derivatives. The reaction preferably takes place in the presence of a water-miscible or immiscible inert organic solvent in the presence or absence of water. Suitable inert organic solvents are e.g. hydrocarbons, such as benzene, toluene or xylene, lower alkanols, such as methanol or ethanol, ether-like liquids, such as ether, dioxane or tetrahydrofuran, chlorinated hydrocarbons, such as methylene chloride, lower ketones, such as acetone or methyl ethyl ketone, carboxylic acid esters, such as ethyl acetate, carboxylic acid nitriles, such as acetonitrile or sulfones, such as tetrahydro-thiophene-1,1-dioxide. The turnover can be carried out in the presence or absence of an acid-binding agent. Suitable acid-binding agents are inorganic bases or salts, e.g. alkali metal hydroxides, alkali metal hydrogen carbonates, alkali metal carbonates or alkali metal phosphates, such as the corresponding sodium or potassium compounds. Furthermore, calcium carbonates as well as calcium phosphates and magnesium carbonate can also be used.

Som utgangsstoff er med den generelle formel VII egner seg slike forbindelser, hvis symboler m, R-^, R2, R« eller R 5 °9 R4 stemmer overens med symbolene som er oppregnet i tilknytning til form-lene I - VII.' En slik gruppe av utgangsstoffer er N-(2-amino-. etyl)-benzensulfonamider, hvis benzenring er substituert med As starting material with the general formula VII, such compounds are suitable, whose symbols m, R-^, R2, R« or R 5 °9 R4 correspond to the symbols listed in connection with the formulas I - VII.' One such group of starting materials is N-(2-amino-.ethyl)-benzenesulfonamides, whose benzene ring is substituted with

alkylamidoresten. the alkyl amido residue.

i para-stilling. in para position.

El^er en fjerde fremgangsmåte ifolge oppfinnelsen fremstiller man forbindelser med den generelle formel I, idet man kondenserer en forbindelse med den generelle formel VIII, Alternatively, a fourth method according to the invention is to prepare compounds of the general formula I, by condensing a compound of the general formula VIII,

hvor m, og R^ har den under formel I angitte betydning, med en reaksjonsdyktig ester av en hydroksyforbindelse med den generelle formel IX, where m, and R^ have the meaning indicated under formula I, with a reactive ester of a hydroxy compound of the general formula IX,

hvor R, og R ? har den under formel I angitte betydning, under ringslutning og overforer eventuelt den erholdte forbindelse med.en uorganisk eller organisk syre til et addisjonssa 11. where R, and R ? has the meaning given under formula I, during cyclization and optionally transfers the obtained compound with an inorganic or organic acid to an addition sa 11.

Egnede reaksjonsdyktige estere av hydroksyforbindelser med den generelle formel IX er f.eks. halogenider, spesielt klorider eller bromider, videre sulfonsyreestere, f.eks. o- eller p-toluensulfonsyreesteren eller metansulfonsyreester en. Kondensasjonen finner fortrinnsvis sted i et med vann blandbart eller ikkeblandbart opplosningsmiddel i nær- eller fravær av vann. Som opplosningsmidler kan alkanoler, f.eks. butanol, eterlignende varsker, f.eks. dioksan, di etyl eng lyko Imonome t yl e ter , karboksylsyreamider, som N ,N-dirrietylf ormamid eller sulfoksyder, som dirnetylsulfoksyd anvendes. Det er fordelaktig å foreta kondensasjonen i nærvær av et syrebindende middel. Som slike kan anvendes de forbindelser, som er nevnt i tilknytning til den tredje fremgangsmåte, videre også tertiære organiske baser, som f.eks. N ,N-diisopropyl-etylamin. Suitable reactive esters of hydroxy compounds with the general formula IX are e.g. halides, especially chlorides or bromides, further sulphonic acid esters, e.g. the o- or p-toluenesulfonic acid ester or methanesulfonic acid ester a. The condensation preferably takes place in a water-miscible or immiscible solvent in the presence or absence of water. As solvents, alkanols, e.g. butanol, ether-like solvents, e.g. dioxane, diethyl eng lyco Imonome t yl ether, carboxylic acid amides, such as N,N-dirrietylf ormamide or sulfoxides, such as dirnethyl sulfoxide are used. It is advantageous to carry out the condensation in the presence of an acid-binding agent. As such, the compounds mentioned in connection with the third method can be used, as well as tertiary organic bases, such as e.g. N,N-diisopropyl-ethylamine.

Som utgangsprodukter ved den fjerde fremgangsmåte kan f.eks. de foran oppregnede reaksjonsdyktige estere av en hydroksyforbindelse med den generelle formel IX anvendes, hvis symboler R-^ og R2 stemmer overens med symbolene som er oppregnet i tilknytning til formel I. En gruppe av bromider med den generelle formel IX kan. f.eks. oppnås, når man omsetter 1-alkyl-aziridiner [sml. As output products in the fourth method, e.g. the previously listed reactive esters of a hydroxy compound of the general formula IX are used, whose symbols R-^ and R 2 correspond to the symbols listed in connection with formula I. A group of bromides of the general formula IX can. e.g. is obtained, when one reacts 1-alkyl-aziridines [cf.

A. Weissberger, Heterocyclic Compounds with Three and Four-Membered Rings, Part One, John Wiley Sons Inc., London (1964)] A. Weissberger, Heterocyclic Compounds with Three and Four-Membered Rings, Part One, John Wiley Sons Inc., London (1964)]

med bromcyan i dioksan. with cyanogen bromide in dioxane.

Eiter en femte fremgangsmåte ifblge oppfinnelsen fremstiller man forbindelser med den generelle formel I, idet man kondenserer en reaksjonsdyktig ester av en forbindelse med den generelle formel X, According to a fifth method according to the invention, compounds of the general formula I are prepared by condensing a reactive ester of a compound of the general formula X,

hvor m, R^, R« og R^ har den under formel I angitte where m, R^, R« and R^ have the under formula I indicated

be tyd-n Ing, be tyd-n Ing,

med et amin med den generelle formel XI, with an amine of the general formula XI,

hvor R^ har den under formel I angitte betydning, where R^ has the meaning given under formula I,

og cykliserer og overforer eventuelt den erholdte forbindelse med en. uorganisk eller organisk syre til el. addis jonssalt. and cyclizes and optionally transfers the obtained compound with a. inorganic or organic acid for electricity. addis jon salt.

Egnede reaksjonsdyktige estere av en hydroksyf orbind-else med den generelle formel X er f.eks. halogenider, spesielt klorider eller bromider eller sulfonsyreestere, spesielt en benzensul-fonsyreester, som i p-stilling er substituert med amidoalkyl- Suitable reactive esters of a hydroxy compound with the general formula X are e.g. halides, especially chlorides or bromides or sulfonic acid esters, especially a benzenesulfonic acid ester, which is substituted in the p-position with amidoalkyl-

res ten- res ten-

Kondens asjonen foretas fortrinns- Condensation is carried out preferentially

vis i et oppiosn ingsmiddel . bom slike egner seg, t.eks. de samme-opplosningsmidler som anvendes ved fjerde fremgangsmåte. show in an opiate agent. bom such are suitable, e.g. the same solvents used in the fourth method.

Det er fordelaktig å foreta omsetningen i nærvær av et syrebindende middel. Som syrebindende midler egner seg. fortrinnsvis baser med den geaerelle formel XI I overskudd. It is advantageous to carry out the turnover in the presence of an acid-binding agent. Suitable as acid-binding agents. preferably bases of the general formula XI in excess.

Som utgangsstoffer ved denne fremgangsmåte egner seg f.eks. de foran oppregnede reaksjonsdyktige estere av hydroksyforbindelser med den generelle formel X, hvis symboler m, R,-,, R^ og R 4 stemmer overens med symbolene som er oppregnet i tilknytning til formel I. Suitable starting materials for this method are e.g. the previously listed reactive esters of hydroxy compounds of the general formula X, whose symbols m, R,-,, R^ and R 4 correspond to the symbols listed in connection with formula I.

En'gruppe av slike forbindelser fremstilles f.eks. som folger: Man går ut fra aziridin og omsetter dette med bromcyan i eter til N-(2-brom-etyl)-cyanamidet; dette cyanamid kondenserer man i aceton med et benzensulfonylklorid, hvilket i p-stilling er substituert med resten i nærvær av for-tynnet natronlut under avspaltning av hydrogenklorid til et tilsvarende N-(2-brom-etyl)-N-cyanobenzensulfonamid. Etter en sjette fremgangsmåte når nye derivater av l-(p-amino-alkyl-fenylsulfonyl)-2-imino-imidazolidin med den generelle formel I, hvor R- dog bare kan bety hydrogen, skal fremstilles, formylerer man forbindelser med den generelle formel XII, A group of such compounds is produced, e.g. as follows: One starts from aziridine and reacts this with cyanogen bromide in ether to form the N-(2-bromoethyl)-cyanamide; this cyanamide is condensed in acetone with a benzenesulfonyl chloride, which is substituted in the p-position with the residue in the presence of dilute caustic soda with splitting of hydrogen chloride to a corresponding N-(2-bromoethyl)-N-cyanobenzenesulfonamide. According to a sixth method, when new derivatives of l-(p-amino-alkyl-phenylsulfonyl)-2-imino-imidazolidine with the general formula I, where R- can however only mean hydrogen, are to be prepared, compounds with the general formula are formylated XII,

hvor m, R^, R2 og R^ har den under formel I angitte where m, R^, R2 and R^ have the under formula I indicated

betydning, importance,

med kloral og overforer eventuelt de erholdte forbindelser med en uorganisk eller organisk syre til et addisjonssalt. Formyl-eringen finner sted ifolge Blicke, Am. Soc. 74, 3933 (1952) i et inert opplosningsmiddel, f.eks. i dioksan, tetrahydrofuran, benzen, toluen eller et klorert hydrokarbon, som f.eks. metylen-klorid. with chloral and optionally transfer the compounds obtained with an inorganic or organic acid to an addition salt. The formylation takes place according to Blicke, Am. Soc. 74, 3933 (1952) in an inert solvent, e.g. in dioxane, tetrahydrofuran, benzene, toluene or a chlorinated hydrocarbon, such as e.g. methylene chloride.

Utgangsstoffer med den generelle formel XII oppnås etter de i tilknytning til den andre fremgangsmåte , beskrevne metoder, fortrinnsvis ved hydrolyse av de tilsvarende substituerte l-[p-(2-acetamido-alkyl)-fenylsulfonyl]-2-imino-imidazolidiner med den generelle formel Ia. Starting substances with the general formula XII are obtained according to the methods described in connection with the second method, preferably by hydrolysis of the correspondingly substituted 1-[p-(2-acetamido-alkyl)-phenylsulfonyl]-2-imino-imidazolidines with the general formula Ia.

De1etter fremgangsmåten ifolge oppfinnelsen erholdte forbindelser med den generelle formel I overfores deretter, hvis dnsket, til deres salter med uorganiske såvel som organiske syrer. Fremstillingen av disse salter finner f.eks. sted ved omsetning av forbindelser med den generelle formel I med den ekvivalente mengde av en syre i et egnet vandig-organisk eller organisk opplosningsmiddel, som f.eks. metanol, etanol, dietyleter, kloroform eller metyl enklorid. The compounds of the general formula I obtained by the process according to the invention are then transferred, if desired, to their salts with inorganic as well as organic acids. The production of these salts can be found e.g. place by reacting compounds of the general formula I with the equivalent amount of an acid in a suitable aqueous-organic or organic solvent, such as e.g. methanol, ethanol, diethyl ether, chloroform or methylene chloride.

Til anvendelse som legemidler kan i stedet for de frie forbindelser med den generelle formel I deres farmasoytisk aksepter-bare salter med syrer anvendes. Egnede addisjonssalter er f.eks. salter med klorhydrogensyre, bromhydrogensyre, svovel-syre,, f os f o rs yre , me tans u 1 f ons yre , etansulfonsyre,- (3-hydroksy-etansulfonsyre, eddiksyre, melkesyre, oksalsyre, ravsyre, fumarsyre, maleinsyre, eplesyre, vinsyre, sitronsyre, salicyl-syre, f enyl edd iksyre, mandelsyre og ernbonsyre, såvel som salter med blodsukkersenkende sulfon-ylkarbamider, som f.eks. p-toluensulfonyl-butyl-karbaniid, p-klorbenzensulfonyl-propyl-k a r barn id , p-[2-(2-metoksy-5-klorbenzamido)-etyl]-fenylsulfonyl-cykloheksylkarbamid. For use as pharmaceuticals, instead of the free compounds of the general formula I, their pharmaceutically acceptable salts with acids can be used. Suitable addition salts are e.g. salts with hydrochloric acid, hydrobromic acid, sulfuric acid , citric acid, salicylic acid, phenylacetic acid, mandelic acid and ernbonic acid, as well as salts with blood sugar-lowering sulphonyl ureas, such as p-toluenesulphonyl-butyl-carbaniide, p-chlorobenzenesulphonyl-propyl-carbenid, p -[2-(2-Methoxy-5-chlorobenzamido)-ethyl]-phenylsulfonyl-cyclohexylurea.

De nye aktivstoffer administreres fortrinnsvis peroralt. De daglige doser beveger seg mellom 30 og 300 mg for voksne pasi-enter med normal vekt. Egnede doseenhetsformer,. som drageer, tabletter inneholder fortrinnsvis 30 - 300 mg av et aktivstoff ifolge oppfinnelsen og da 20 til .80 % aven forbindelse med den generelle formel I. The new active substances are preferably administered orally. The daily doses range between 30 and 300 mg for adult patients of normal weight. Suitable dosage unit forms,. as dragees, tablets preferably contain 30 - 300 mg of an active substance according to the invention and then 20 to .80% of the compound with the general formula I.

Den hypoglykemiske virkning for folgende substanser ble under-sokt: 1. l-sulfanilyl-2-imino-3-n-butyI-imrdazolidin (ifolge soknacT nr. 167.442) 2. l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-n-butyl-imidazolidin (ifolge nærværende oppfinnelse) 3. l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-n-butyl-4-etyl-imidazolidin (ifolge nærværende oppfinnelse) 4. l-[p-(2-valerylamido-etyl)-fenylsulfonyl]-2-imino-3-n-butyl-imidazolidin (ifolge nærværende oppfinnelse) 5. 1-[p-(2-isovalerylamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin (ifolge nærværende oppfinnelse) 6. l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin (ifolge nærværende oppfinnelse) 7. l-[p-[_2- (3-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin (ifolge nærværende oppfinnelse) 8. l-[p-(2-cyklopropankarboksamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin (ifolge nærværende oppfinnelse) 9. l-[p-(2-cykloheksankarboksamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin (ifolge nærværende oppfinnelse. The hypoglycaemic effect of the following substances was investigated: 1. 1-sulfanyl-2-imino-3-n-butyl-imrdazolidine (according to soknacT no. 167,442) 2. 1-[p-(2-acetamido-ethyl)- phenylsulfonyl]-2-imino-3-n-butyl-imidazolidine (according to the present invention) 3. l-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-n-butyl-4-ethyl -imidazolidine (according to the present invention) 4. 1-[p-(2-valerylamido-ethyl)-phenylsulfonyl]-2-imino-3-n-butyl-imidazolidine (according to the present invention) 5. 1-[p-(2 -isovalerylamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine (according to the present invention) 6. l-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl] -2-imino-3-isobutyl-imidazolidine (according to the present invention) 7. l-[p-[_2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine (according to present invention) 8. l-[p-(2-cyclopropanecarboxamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine (according to the present invention) 9. l-[p-(2-cyclohexanecarboxamido-ethyl)- phenylsulfo nyl]-2-imino-3-isobutyl-imidazolidine (according to the present invention.

Metode: Method:

Provesubstansene ble ved hjelp av traganth suspendert i led-ningsvann og ved hjelp av en magesonde administrert til rotter som i 6 1/2 timer ikke hadde mottatt noe fir. Bloduttagningen skjedde fra det retroorbitale veneplexus. Blodsukkeret ble bestemt etter Hagedorn-Jensen i auto-analyzer. The test substances were suspended in tap water by means of tragacanth and administered by means of a gastric tube to rats that had not received any fur for 6 1/2 hours. Blood was drawn from the retroorbital venous plexus. The blood sugar was determined according to Hagedorn-Jensen in an auto-analyzer.

Forsdksresultatene er sammenfattet i nedenstående tabell: The research results are summarized in the table below:

Forsøksresultatene viser at forbindelsene 2-9 som fremstilles ifolge oppfinnelsen har en vesentlig sterkere hypoglykemisk The test results show that the compounds 2-9 produced according to the invention have a significantly stronger hypoglycaemic

virkning enn forbindelsen 1 som er kjent fra norsk patentsøknad nr. 167.442. effect than compound 1 which is known from Norwegian patent application no. 167,442.

De etterfølgende eksempler redegjor nærmere for fremstillingen av de nye forbindelsene med den generelle formel I og av hittil ikke beskrevne mellomprodukter, men er imidlertid på ingen måte de eneste utforelsesformer av den samme. Temperaturene er an-gitt i Celsiusgrader. The following examples explain in more detail the preparation of the new compounds of the general formula I and of previously undescribed intermediates, but are by no means the only embodiments of the same. The temperatures are indicated in degrees Celsius.

EKSEMPEL 1 EXAMPLE 1

a) Man tilsetter 17,8 g l-butyl-2-imino-imidazoli.din-hydroklorid til 8,5 g natriumhydroksyd i 85 ml vann. Den erholdte, a) 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride is added to 8.5 g of sodium hydroxide in 85 ml of water. The received,

klare oppldsning tilsettes 26,2 g i 100 ml' aceton opplost p-(2-acetamido-etyl)-benzensulfonylklorid, hvorved reaksjonsbland ingen oppvarmes. Den oppvarmes i 1/.2 time til 90° og inndampes så i vakuum. Man omkrystalliserer resten fra eddiksyreetylester og oppnår det rene 1-[p-(2-acetamido-ety1)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin, som smelter ved 130 - 131°. clear solution, 26.2 g in 100 ml of acetone dissolved in p-(2-acetamido-ethyl)-benzenesulfonyl chloride are added, whereby the reaction mixture is not heated. It is heated for 1/2 hour to 90° and then evaporated in a vacuum. The residue is recrystallized from acetic acid ethyl ester and the pure 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine is obtained, which melts at 130 - 131°.

På analog måte oppnår man fra: Analogously, one obtains from:

16,3 g l-propyl-2-imino-imidazolidin-hydroklorid og 24,8 g p-(formamido-etyl)-benzensulfonylklorid l-[p-(2-formamido-etyl)-fenylsulfonyl]-2-imino-3-propyl-imidazolidinet, smp. 103-104°; 16.3 g of 1-propyl-2-imino-imidazolidine hydrochloride and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3 -propyl-imidazolidine, m.p. 103-104°;

16,3 g l-propyl-2-imino-imidazolidin-hydroklorid og 29,0 g p-(2-butyramido-etyl)-benzensulfonyl-klorid 1-[p-(2-bu tyramido-etyl)-fenylsulfonyl]-2-imino-3-propyl-imidazolidinet, HjO, 16.3 g of 1-propyl-2-imino-imidazolidine hydrochloride and 29.0 g of p-(2-butyramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]- The 2-imino-3-propyl-imidazolidine, HjO,

smp. 114 - 116°; m.p. 114 - 116°;

16,3 g l-isopropyl-2-imino-imidazolidin-hydroklorid og 24,8 g p-(formamido-etyl)-benzensulfonyl-klorid l-[p-(2-formarnido-etyl)-fenylsulfonyl]-2 -imino-3-isopropyl-imidazolidinet, smp. 112 - 113°; 16.3 g of 1-isopropyl-2-imino-imidazolidine hydrochloride and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-formarnido-ethyl)-phenylsulfonyl]-2-imino -3-isopropyl-imidazolidine, m.p. 112 - 113°;

16,3 g l-isopropyl-2-imino-imidazolidin-hydroklorid og 27,6 g p-(2-propionamido-etyl)-benzensulfonyl-klorid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-Isopropyl-imidazolidinet, smp. 111 - 112°_; 16.3 g of l-isopropyl-2-imino-imidazolidine hydrochloride and 27.6 g of p-(2-propionamido-ethyl)-benzenesulfonyl chloride l-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2 -imino-3-Isopropyl-imidazolidine, m.p. 111 - 112°_;

16,3 g l-isop.ropyl-2-imino-imidazolidin-hydroklorid og 29,0 g p-(2-butyramido-etyl)-benzensu1fonyl-klorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, smp. 139 - 140°; 16.3 g of 1-isopropyl-2-imino-imidazolidine hydrochloride and 29.0 g of p-(2-butyramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl] -2-imino-3-isopropyl-imidazolidine, m.p. 139 - 140°;

14,3 g l-butyl-2-imino-imidazolidin og 24,8 g p-(formamido-etyl)-benzensulfonyl-klorid l-[p-(2-formamido-etyl)-fenylsulfo- 14.3 g of l-butyl-2-imino-imidazolidine and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride l-[p-(2-formamido-ethyl)-phenylsulfo-

nyl]-2-imino-3-butyl-imidazolidinet, smp. 111 - 112°; nyl]-2-imino-3-butyl-imidazolidine, m.p. 111 - 112°;

17.7 g l-butyl-2-imino-imidazolidin-hydroklorid og 27,55 g p-(3-acetamido-propyl)-benzensulfonyl-klorid l-[p-(3-acetamido-propy1)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 92 - 93°; 17.7 g l-butyl-2-imino-imidazolidine hydrochloride and 27.55 g p-(3-acetamido-propyl)-benzenesulfonyl chloride l-[p-(3-acetamido-propyl)-phenylsulfonyl]-2-imino -3-butyl-imidazolidine, m.p. 92 - 93°;

14,3 g 1-isobutyl-2-imino-imidazolidin og 24,8 g p-(formamido-etyl)-benzensulfonyl-klorid 1-[p-(2-formamido-etyl)-f enylsulfo-nyl] -2-imino-3-isobutyl-imidazolidinet, smp. 107 - 108°; 14.3 g of 1-isobutyl-2-imino-imidazolidine and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2- imino-3-isobutyl-imidazolidine, m.p. 107 - 108°;

iin

17.8 g 1-butyl-2-imino-imidazolidin-hydroklorid og 27,6 g p-( 2-ac e tårni do-propyl )-benzensulfonyl-klorid l-[p-( 2-acét amido-propyl) - f eny 1 su lf onyl ]-2-imino-3-butyl - imida zo 1 idinet, smp.. 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride and 27.6 g of p-(2-acetamido-propyl)-benzenesulfonyl chloride l-[p-(2-acetamido-propyl)-pheny 1 sulf onyl ]-2-imino-3-butyl - imida zo 1 idine, m.p..

120 - 122°; 120 - 122°;

17,8 g l-butyl-2-imino-imidazolidin-hydroklorid og 27,6 g p-(2-propionamido-etyl)-ben zen sul fonyl-klorid l-[p-(2-propionamido-etyl)- fenylsulfonyl]-2-imino-3-buty1- imidazolid inet, 17.8 g of l-butyl-2-imino-imidazolidine hydrochloride and 27.6 g of p-(2-propionamido-ethyl)-benzenesulfonyl chloride l-[p-(2-propionamido-ethyl)-phenylsulfonyl ]-2-imino-3-buty1- imidazolidinate,

smp. 137 - 138°; m.p. 137 - 138°;

17,8 g l-butyl-2-imino-imidazolid'in-hydroklorid og 28,9 g p-(2-butyramido-etyl)-benzensulfonyl-klorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 123. - 124°; 17.8 g of 1-butyl-2-imino-imidazolidin hydrochloride and 28.9 g of p-(2-butyramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl] -2-imino-3-butyl-imidazolidine, m.p. 123. - 124°;

17,8 g 1-bu tyl-2-imino-imidazolidin-hydroklorid og- 27,6 g- p-•(2-a-metylbut.yramido-etyl)-benzensulfonyl-klorid l-[p-(2-oc-metylbutyramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazoli-diuet, smp. 114 - 116°; 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride and 27.6 g of p-•(2-a-methylbut.yramido-ethyl)-benzenesulfonyl chloride l-[p-(2-oc -methylbutyramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazoli-diuet, m.p. 114 - 116°;

17,8 g l-butyl-2-imino-imidazolidin-hydroklorid og 30,4 g p-(2-valeramido-etyl)-benzensulfonylklorid l-[p-(2-valeramido-etyl)-f enylsu lf onyl]-2-imino-3-bu tyl-imidazol idinet,. smp. 130°; 17.8 g of l-butyl-2-imino-imidazolidine hydrochloride and 30.4 g of p-(2-valeramido-ethyl)-benzenesulfonyl chloride l-[p-(2-valeramido-ethyl)-phenylsulfonyl]- 2-imino-3-butyl-imidazole idine,. m.p. 130°;

22,2 g l-isobutyl-2-imino-imidazolidin-hydrobromid og 26,15 g p-(2-acetamido-etyl)-benzensulfonyl-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 22.2 g of l-isobutyl-2-imino-imidazolidine hydrobromide and 26.15 g of p-(2-acetamido-ethyl)-benzenesulfonyl chloride l-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2 -imino-3-isobutyl-imidazolidine, m.p.

149 - 151° 149 - 151°

22,2 g 1-isobutyl-2-imino-imidazolidin-hydrobromid dg 27,5b g p-(3-acetamido-propyl)-benzensulfonylklorid l-[p-(3-acetamido-propyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, som olje; 22.2 g 1-isobutyl-2-imino-imidazolidine hydrobromide dg 27.5b g p-(3-acetamido-propyl)-benzenesulfonyl chloride 1-[p-(3-acetamido-propyl)-phenylsulfonyl]-2-imino -3-isobutyl-imidazolidine, as oil;

22,2 g l-isobutyl-2-imino-imidazolidin-hydroklorid og 30,4 g p-(2-valeramido-etyl)-benzensulfonyl-klorid l-[p-(2-valeramiHo-et yl) - f enylsu lf onyl] -2-imino-3- i so bu tyl -irn Ldazol idinet, smp. 137 - 140°; 22.2 g of 1-isobutyl-2-imino-imidazolidine hydrochloride and 30.4 g of p-(2-valeramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-valeramiHo-ethyl)-phenylsulph onyl] -2-imino-3- i so butyl -irn Ldazol idine, m.p. 137 - 140°;

22,2 g l-isobutyl-2-imino-imidazolidin-hydroklorid og 39,0 g p-[2-(2-metoksy-5-klor-benzamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-Imidazolidinet, smp. 117,5 - 119°; 22.2 g of l-isobutyl-2-imino-imidazolidine hydrochloride and 39.0 g of p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-benzenesulfonyl chloride l-[p-[2 -(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-Imidazolidine, m.p. 117.5 - 119°;

22,2 g l-isobutyi-2-imino-imidazolidin-hydroklorid og 33,0 g p-(2-cykloheksan-karbamido-etyl)-benzensulfonyl-klorid 1 - [ p-[2-(cykloneksan-kårbok samido)-etyl]-fenylsulfonyl]-2-imlno-3-isobutyl-imidazolidinet, smp. 175 - 177°; 22.2 g of 1-isobutyl-2-imino-imidazolidine hydrochloride and 33.0 g of p-(2-cyclohexane-carbamido-ethyl)-benzenesulfonyl chloride 1-[p-[2-(cyclonexane-carbamido)- ethyl]-phenylsulfonyl]-2-imlno-3-isobutyl-imidazolidine, m.p. 175 - 177°;

17,75 g 1-s ek ..bu tyl-2-imino-imidazo lid in-hydrok lor id og 26,15 g p-(2-acetamido-etyl)-benzensulfonyl-klorid l-[p-(2-acetamido - ety1)- f enylsul fonyl]-2-imino-3-sek.butyl-imidazo1 id inet, smp. 106 - 108°} 17.75 g of 1-sec ..butyl-2-imino-imidazolidin hydrochloride and 26.15 g of p-(2-acetamido-ethyl)-benzenesulfonyl chloride 1-[p-(2- acetamido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazo1 id inet, m.p. 106 - 108°}

17,8 g 1-sek.butyl-2-imino-imidazolIdin-hydroklorid og 27,6 g p-(2-propionamldo-etyl)-benzensulfonyl-klorid l-[p-(2-propionamido- etyl) - f en yl sulf on yl] -2 - imino-3-s ek .bu tyl - irn ida zo 1 idinet, smp. 17.8 g of 1-sec.butyl-2-imino-imidazolidine hydrochloride and 27.6 g of p-(2-propionamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-propionamido-ethyl)-f en yl sulfon yl] -2 - imino-3-s ec .but yl - irn ida zo 1 idinet, m.p.

17,8 g 1 sek.butyl-2-imino-imidazolldih-hydroklorid og 29,0 g p- ( 2-bu ty r am ido - etyl) - benzensulfonyl-k lorid 1 -[ p- ("2- bu tyr am ido - etyl)-f enylsulfonyl]-2-imino-3-s ek.butyl-imidazo1 id inet, smp. 17.8 g of 1 sec.butyl-2-imino-imidazoldih-hydrochloride and 29.0 g of p-(2-butyramido-ethyl)-benzenesulfonyl-chloride 1-[p-("2-butyr amido - ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazo1 id inet, m.p.

22,2 g 1-tert.butyl-2-imino-imidazolidin-hydrobromid og 26,15 g 22.2 g of 1-tert.butyl-2-imino-imidazolidine hydrobromide and 26.15 g

p-(2-acetamido-etyl)-benzensulfonyl-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 129 - 130°; p-(2-acetamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-tert-butyl-imidazolidine, m.p. 129 - 130°;

22,2 g 1-tert.bu tyl-2-imino-imidazo1 idin-hydroklorid og 29,0 g p-(2-isovalerami.do-etyl)-benzensulfonylklorid l-[p-(2-isovaler-amido-e ty1)- fenylsulfon yl]-2-imino-3-tert.butyl-imida zolidin e t, smp. 152 - 154 °-, 22.2 g of 1-tert.butyl-2-imino-imidazo1idine hydrochloride and 29.0 g of p-(2-isovaleramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-isovaler-amido-e ty1)-phenylsulfonyl]-2-imino-3-tert.butyl-imida zolidine e t, m.p. 152 - 154 °-,

15,5 g 1-cykLopenty1-imino-imidazolidin og 24,8 g p-(formamido-etyl)-benzensulfonyl-klorid l-[p-(2-formamido-etyl)-fenylsulfo-nyl]-2-imino-3-cyklopentyl-imidazolid inet, smp. 108 - 110°; 15.5 g of 1-cyclopentyl-imino-imidazolidine and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3 -cyclopentyl-imidazolidinate, m.p. 108 - 110°;

18,97 g 1-cyklopentyl-2-imino-imidazolidin-hydroklorid og 26,1b g p-(?.-acetamido-etvl)-benzensulfonylklorid l-[p-(2-acetamido-e tyl)- f eny1 su i fony1J-2-imino-3-cyklopen tyl-imidazolidinet, smp. 151 - 152°; 18.97 g of 1-cyclopentyl-2-imino-imidazolidine hydrochloride and 26.1 g of p-(?-acetamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-acetamido-ethyl)-phenylsu i phony1J-2-imino-3-cyclopen tyl-imidazolidine, m.p. 151 - 152°;

18,9 g 1-cyk1 open ty1-2-imino-Imidazolid in-hydroklorid og 29,0 g p-(2-bu tyramIdo-etyl)-ben z ensulf onyl-klorid 1 - [ p - ( 2- bu tyrarnido - etyl)-fenylsulfonyl|-2-imlno-3-cyklopen ty1-imidazolid in e t, 18.9 g of 1-cyc1 open ty1-2-imino-Imidazolidin hydrochloride and 29.0 g of p-(2-butyramido-ethyl)-benz ensulfonyl chloride 1 - [ p - ( 2- bu tyranido - ethyl)-phenylsulfonyl|-2-imlno-3-cyclopenethy1-imidazolidin e t,

smp. m.p.

20,5 g 1-cykloheksyl-2-imino-imidazo1idin-hydroklorid og 24,8 g p-(2-f ormamido-e tyl)-benzensulfonyl-klorid 1-[p-(2-f ormamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 135 - 136°; 20.5 g of 1-cyclohexyl-2-imino-imidazo1idine hydrochloride and 24.8 g of p-(2-formamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-formamido-ethyl)-phenylsulfonyl ]-2-imino-3-cyclohexyl-imidazolidine, m.p. 135 - 136°;

20,37 g 1-cykloheksyl-2-imino-imidazolidin-hydroklorid og 2u,15 g p-(2-acetamido-etyl)-benzensulfonyl-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 181 - 183°; 20.37 g of 1-cyclohexyl-2-imino-imidazolidine hydrochloride and 2u.15 g of p-(2-acetamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2 -imino-3-cyclohexyl-imidazolidine, m.p. 181 - 183°;

20,37 g l-eykloheksyl-2-imino-imidazolidin-hydroklorid og 29,0 g p-[2-(N-metyl-acetamido)propyl]-benzensulfonyl-klorid l-[p-[2-(N-metyl-acetamido)-propyl]-f enylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 108 - 110°; 20.37 g of 1-cyclohexyl-2-imino-imidazolidine hydrochloride and 29.0 g of p-[2-(N-methyl-acetamido)propyl]-benzenesulfonyl chloride 1-[p-[2-(N-methyl -acetamido)-propyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 108 - 110°;

21,8 g l-cykloheksyl-4-metyl-2-imino-imidazolidin-hydxoklorid og 29.0 g p-(2-butyramido-etyl)-benzensulfonyl-klorid l-[p-(2-butyramido-etyl) - f enylsulfonyl] -2-imino-3-cyk loheksyl-5-rnetyl-imidazo1 idinet, smp. 109 - 111°; 21.8 g of 1-cyclohexyl-4-methyl-2-imino-imidazolidine hydrochloride and 29.0 g of p-(2-butyramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl ] -2-imino-3-cyclohexyl-5-methyl-imidazo1idine, m.p. 109 - 111°;

20*5 g l-cykloheksyl-2-imino-imIdazolidin-hydroklorid og 30,4 g p-(2-valeramido-etyl)-ben zensulfonyl-klor id 1-[p-(2-va 1eramido - etyl)-f enylsu1 fonyl]-2-imino-3-cykloheksyl-imidazolid inet, 20*5 g of 1-cyclohexyl-2-imino-imidazolidine hydrochloride and 30.4 g of p-(2-valeramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-va1eramido-ethyl)-f enylsulfonyl]-2-imino-3-cyclohexyl-imidazolidinate,

1/4 H90, smp. 154 - 155°; 1/4 H90, m.p. 154 - 155°;

20,5 g l-cykloheksyl-2-imino-irnidazolidin-hydrok lorid og 30,4 g p-(2-isovaleramido-etyl)-benzensulfonyl-klorid l-[p-(2-isova-1eramido-etyl)-fenylsul fonyl]-2-imino-3-cykloheksyl- lmIdazo1 i - dinet,'smp. 180 - 181°; 20.5 g of 1-cyclohexyl-2-imino-irnidazolidine hydrochloride and 30.4 g of p-(2-isovaleramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-isova-1eramido-ethyl)-phenylsul phenyl]-2-imino-3-cyclohexyl- lmIdazo1 i - dinet, m.p. 180 - 181°;

20,5 g l-cykloheksyl-2-imino-imidazo1 idin-hydroklorid og 33,0 g p-(2-cykloheksankårboksamido-etyl)-benzensulfonyl-klorid 1 - [ p-(2-cykloheksankarboksamIdo-etyl)-fenyl-sulfonyl]-2-Imlno-3-cykloheksyl-imidazolidinet, smp. 208 - 209°; 20.5 g of 1-cyclohexyl-2-imino-imidazo-1-idine hydrochloride and 33.0 g of p-(2-cyclohexanecarboxamido-ethyl)-benzenesulfonyl chloride 1- [ p-(2-cyclohexanecarboxamido-ethyl)-phenyl-sulfonyl ]-2-Imlno-3-cyclohexyl-imidazolidine, m.p. 208 - 209°;

20,37 g l-cykloheksyl-2-imino-imidazolidin-hydroklor Id og 35,4 g p-[2-(m-metoksy-benzamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(m-metoksy-benzamido)- etyl]- fenylsulfonyl]-2-imino-3-cykloheksyl-imidazol idinet, smp. 167 - 168°; 20.37 g of 1-cyclohexyl-2-imino-imidazolidine hydrochloride Id and 35.4 g of p-[2-(m-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride l-[p-[2-(m -methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazole idine, m.p. 167 - 168°;

18.1 g l-cykloheptyl-2-imino-imidazolIdi-n og 24,8 g.p-(forrn-amido-etyl)-benzensul fonyl-klorid l-[p-(2-formamido-etyl)-f enylsulfonyl]-2-imino-3-cykloheptyl-Imidazol idinet, srnp. 130 - 133°; 18.1 g of 1-cycloheptyl-2-imino-imidazolIdi-n and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2- imino-3-cycloheptyl-Imidazole idine, srnp. 130 - 133°;

21,77 g 1-cykloheptyl-2-imino-imidazolidin-hydroklorid og 26,15 g p-(2-acetamido-etyl)-benzensu1 fonyl-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cyklohepty1-imidazo1idinet, smp. 166 - 167°; 21.77 g of 1-cycloheptyl-2-imino-imidazolidine hydrochloride and 26.15 g of p-(2-acetamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]- 2-imino-3-cyclohepty1-imidazo1idine, m.p. 166 - 167°;

21,8 g l-cykloheptyl-2-imino-imidazolidin-hydroklorid og" 29,0 g p-{2-butyramido-etyl)-benzensulfonyl-klorid 1-[p-(2-bu tyramido-etyl )- f enylsulfonyl]-2-imino-3-cyklohepty1-imidazolidinet, 21.8 g of 1-cycloheptyl-2-imino-imidazolidine hydrochloride and 29.0 g of p-{2-butyramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl ]-2-imino-3-cycloheptyl-imidazolidine,

smp. m.p.

23,6 g l-butyl-o-metyl-2-imino-imidazolidin--hydrobromid og 26,1b g p-(2-acetamido-etyl)-benzensu lfonyl-Rlorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidinet, smp. 132 - 133°; 23.6 g of l-butyl-o-methyl-2-imino-imidazolidine hydrobromide and 26.1 g of p-(2-acetamido-ethyl)-benzenesulfonyl chloride l-[p-(2-acetamido-ethyl) )-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine, m.p. 132 - 133°;

2b ,0 g 1-butyl-b-etyl-2-imino-imidazolidin-hydrobromid og 26,1b g p-(2-acelamido-etyl)-benzensulfonylklorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-etyl-imidazolidinet, smp. 111 - 114°; 2b .0 g 1-butyl-b-ethyl-2-imino-imidazolidine hydrobromide and 26.1b g p-(2-acelamido-ethyl)-benzenesulfonyl chloride l-[p-(2-acetamido-ethyl)-phenylsulfonyl] -2-imino-3-butyl-4-ethyl-imidazolidine, m.p. 111 - 114°;

19,2 g 1-butyl-4-metyl-2-imino-imidazolidin-hydroklorid og 26.2 g p-(2-acetamido-etyl)-benzens ulfonyl-klorid l-[p-(2-ace tam Ido-etyl)- f enylsu 1 fonyl]-2-imino-3-bu tyl-5-metyl-imidazolidinet, smp. 98 - 99°; 19.2 g of 1-butyl-4-methyl-2-imino-imidazolidine hydrochloride and 26.2 g of p-(2-acetamido-ethyl)-benzene sulfonyl chloride 1-[p-(2-acetamido-ethyl) - phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 98 - 99°;

23,6 g 1-bu ty1-5-etyl-2-imino-imidazolidin-hydrobromid og 30,4 g p-(2-valeramido-etyl)-benzensu lfonylklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-etyl-imidazo-iidinet, smp. 92 - 94°; 23.6 g of 1-butyl-5-ethyl-2-imino-imidazolidine hydrobromide and 30.4 g of p-(2-valeramido-ethyl)-benzenesulfonyl chloride 1-[p-(2-valeramido-ethyl)- phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazo-iidine, m.p. 92 - 94°;

18.3 g 1-( 2-metyl-cykloheksyl)-2-imino-imidazol.idin og 24,8 g p-(f ormamido-etyl)-benz ens ul fonyl-klorid l-[p-(2-formamido-e tyl) - f en yl sul f onyl]'-2- im lno-3 - ( 2-met.yl-cyk loheksyl) - imida zolidinet, smp. 127 - 129°; 18.3 g 1-(2-methyl-cyclohexyl)-2-imino-imidazolidine and 24.8 g p-(formamido-ethyl)-benz ensulfonyl chloride 1-[p-(2-formamido-e tyl)-phenylsulfonyl]'-2-im lno-3 - ( 2-methyl-cyclohexyl)-imida zolidine, m.p. 127 - 129°;

18.3 g 1-(4-metylcykloheksyl)-2-imino-imidazolidin og 24,8 g. p- ( f orm a mi do - etyl )-benzensulfonyI-klorid l-[p- (.2-f ormamido-etyl) -f enylsulfonyl]-2-imino-3-(4-metyl-cykloheksyl)-imidazolidinet, smp. 126 - 128°; 18.3 g of 1-(4-methylcyclohexyl)-2-imino-imidazolidine and 24.8 g of p-(formamido-ethyl)-benzenesulfonyl chloride 1-[p-(.2-formamido-ethyl) -phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexyl)-imidazolidine, m.p. 126 - 128°;

26.4 g 1-(4-metyl-cykloheksyl)-2-imino-imidazolidin-hydroklorid og 26,2 g p-(2-acetamido-etyl)-benzensulfonyl-klorid l-[p-(2-ac et am ido-et yl) - f erryl sul fonyl] -2-imino-3- (4-met yl-cyk loheksyl )-imidazolid-inet., smp.. 166 - 167°. 26.4 g 1-(4-methyl-cyclohexyl)-2-imino-imidazolidine hydrochloride and 26.2 g p-(2-acetamido-ethyl)-benzenesulfonyl chloride 1-[p-(2-ac et amido- etyl)-ferryl sulfonyl]-2-imino-3-(4-methyl-cyclohexyl)-imidazolidin., m.p. 166 - 167°.

Det som utgangsprodukt anvendte p-(2-acetamido-etyl)-benzensul- The starting product used p-(2-acetamido-ethyl)-benzenesul-

fonyl-klorid fremstilles som folger: phenyl chloride is prepared as follows:

b) 16,3 g N-fenetyl-acetamid tilsettes porsjonsvis under roring til 35,0 g klorsulfonsyre. Deretter rores blandingen i 3 b) 16.3 g of N-phenethyl acetamide is added in portions while stirring to 35.0 g of chlorosulfonic acid. The mixture is then stirred in 3

timer ved 60°, hvorpå den helles på is. Krystallene nutsjes fra, vaskes med vann og torkes i vakuum. Det erholdte p-(2-acetamido-etyl)-benzensulfonyl-klorid viderearbeides som råprodukt. hours at 60°, after which it is poured onto ice. The crystals are removed, washed with water and dried in a vacuum. The p-(2-acetamido-ethyl)-benzenesulfonyl chloride obtained is further processed as a crude product.

På analog måte oppnår man de som utgangsstoffer anvendte sulfonylklorider, hvilke forarbeides videre som råprodukter: Fra 14,9 g N-fenetyl-formamid og 35,0 g klorsulfonsyre p-(2-formamido-etyl)-benzensulfonyl-kloridet; In an analogous manner, the sulfonyl chlorides used as starting materials are obtained, which are further processed as raw products: From 14.9 g of N-phenethylformamide and 35.0 g of chlorosulfonic acid p-(2-formamido-ethyl)-benzenesulfonyl chloride;

fra 17,7 g 1-fenyl-2-acetamido-propan og 35,0 g klorsulfonsyre p-(2-acetamido-propyl)-benzensulfonyl-kloridet; from 17.7 g of 1-phenyl-2-acetamido-propane and 35.0 g of the chlorosulfonic acid p-(2-acetamido-propyl)-benzenesulfonyl chloride;

fra 18,7 g N-(3-fenyl)-acetamid og 35,0 g klorsulfonsyre p-(3-acetamido-propyl)-benzensul fonyl-kloridet; from 18.7 g of N-(3-phenyl)-acetamide and 35.0 g of the chlorosulfonic acid p-(3-acetamido-propyl)-benzenesulfonyl chloride;

fra 19,1 g N-( 3-fenyl-propyl)-N-metylacetamid og 35,0 g klorsulfonsyre p-[2- (N-metylacetamido-propy 1") ]- ben zen sul f onyl-kloridet; from 19.1 g of N-(3-phenyl-propyl)-N-methylacetamide and 35.0 g of the chlorosulfonic acid p-[2-(N-methylacetamido-propyl)]-benzenesulfonyl chloride;

fra 17,7 g N-fenetyl-propionamid og 35,0 g klorsulfonsyre p-(2-propionamido-etyl)-benzensulfonyl-kloridet; from 17.7 g of N-phenethyl-propionamide and 35.0 g of the chlorosulfonic acid p-(2-propionamido-ethyl)-benzenesulfonyl chloride;

fra 19,1 g N-fenetyl-butyramid og 50,0 g klorsulfonsyre p-(2-butyramido-etyl)-benzensulfonyl-kloridet; from 19.1 g of N-phenethyl-butyramide and 50.0 g of the chlorosulfonic acid p-(2-butyramido-ethyl)-benzenesulfonyl chloride;

fra 20,5 g N-fenyletyl-valeramid og 35,0 g klorsulfonsyre p-(2-valeramido-etyl)-benzensul fonyl-kloridet; from 20.5 g of N-phenylethyl-valeramide and 35.0 g of the chlorosulfonic acid p-(2-valeramido-ethyl)-benzenesulfonyl chloride;

fra 20,5 g N-fenyletyl-isovalerarnid og 35,0 g klorsulfonsyre p-(2-isova1eramidoetyl)-benzensulfonylkloridet; from 20.5 g of N-phenylethyl isovaleranide and 35.0 g of the chlorosulfonic acid p-(2-isovaleramidoethyl)-benzenesulfonyl chloride;

fra 23,1 g N-fenyletyl-cykloheksan-karbamid og 35,0 g klorsul— from 23.1 g of N-phenylethyl-cyclohexane-urea and 35.0 g of chlorsul—

fonsyre p-(2-cykloheksan-karbamido-etyl)-benzensulfonyl-k loridet. phonic acid p-(2-cyclohexane-carbamido-ethyl)-benzenesulfonyl chloride.

EKSEMPEL 2 EXAMPLE 2

a) Analogt eksempel la) oppnår man fra 17,8 g l-butyl-2-imino-imidazolidin-hydroklorid i natronlut og 35,8 g p-[2-(o-klor-b en z am ido)- etyl]- ben zen sul fon yl-kl or id l-[p-[2-(o-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet med smp. a) Analogous example la) is obtained from 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride in caustic soda and 35.8 g of p-[2-(o-chloro-benzamido)-ethyl] - benzene sulfonyl chloride 1-[p-[2-(o-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine with m.p.

155 - 157° (fra isopropano1). 155 - 157° (from isopropano1).

Det som utgangsprodukt anvendte sulfonylklorid fremstilles som folger: b) 17,6 g o-klor-benzoylklorid tilsettes til 20,3 g p-nitro-fenetylamin-hydroklorid i 30 ml 5-n natronlut og 50,0 g is. N-(p-nitro-fenetyl)-o-klor-benzamidet utkrystalliserer. Det nutsjes fra, ettervaskes med vann, tbrkes og anvendes som råprodukt. The sulfonyl chloride used as starting product is prepared as follows: b) 17.6 g of o-chloro-benzoyl chloride is added to 20.3 g of p-nitro-phenethylamine hydrochloride in 30 ml of 5-n caustic soda and 50.0 g of ice. The N-(p-nitro-phenethyl)-o-chloro-benzamide crystallizes out. It is extracted, washed with water, dried and used as a raw product.

c) 30,5 g av den etter b) erholdte nitroforbindelse suspenderes i 8b mi etanol, tilsettes 1 ml konsentrert saltsyre og kokes med c) 30.5 g of the nitro compound obtained according to b) is suspended in 8 ml of ethanol, 1 ml of concentrated hydrochloric acid is added and boiled with

16,0 g jernpulver i 12 timer under tilbakelop. Deretter filtrerer man reaksjonsblandingen og ettervasker med etanol. Fil-tratet inndampes i vakuum, og resten tilsettes etanolisk saltsyre. Man oppnår N-(p-amino-fenetyl)-o-klor-benzamid-hydroklor-idet, som anvendes som råprodukt. 16.0 g iron powder for 12 hours under reflux. The reaction mixture is then filtered and washed with ethanol. The filtrate is evaporated in vacuo, and ethanolic hydrochloric acid is added to the residue. N-(p-amino-phenethyl)-o-chloro-benzamide hydrochloride is obtained, which is used as a crude product.

d) 31,0 g av det etter c) erholdte hydroklorid tilsettes i 100 ml iseddik og 34 ml konsentrert saltsyre. Man diazoterer d) 31.0 g of the hydrochloride obtained after c) is added to 100 ml of glacial acetic acid and 34 ml of concentrated hydrochloric acid. One diazotizes

oppiosningen ved 5° med 7,6 g natriumnitrit, som er opplost i 30 ml vann. Den erholdte diazoniumsaltopplbsning helles i en med svoveldioksyd mettet opplosning av 4,0 g cupriklorid, 7 ml vann og 80 ml iseddik. Æn lett eksoterm reaksjon inntrer, som spaltes fra ved 35° med nitrogen. Man lar reaksjonsblandingen stå i 2 timer. p-[2-(o-klor-benzamido)-etyl]-benzensulfonyl-kloridet utkrystalliserer. Krystallene nutsjes fra og vaskes med vann og anvendes som råprodukt. the solution at 5° with 7.6 g of sodium nitrite, which is dissolved in 30 ml of water. The resulting diazonium salt solution is poured into a sulfur dioxide-saturated solution of 4.0 g of cupric chloride, 7 ml of water and 80 ml of glacial acetic acid. Another slightly exothermic reaction occurs, which is split off at 35° with nitrogen. The reaction mixture is allowed to stand for 2 hours. The p-[2-(o-chloro-benzamido)-ethyl]-benzenesulfonyl chloride crystallizes out. The crystals are extracted and washed with water and used as a raw product.

EKSEMPEL 3 EXAMPLE 3

Analogt eksempel la) oppnår man fra 17,8 g 1-tert.butyl-2-imino-imidazolidin-hydroklorid i natronlut og 35,8 g p-[2-(o-klor-benzamido)-etyl]-benzensulfonylklorid l-[p-[2-(o-klor-benzamido) -etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet med smp. 152 - 154° (fra etanol). Analogously to example la) one obtains from 17.8 g of 1-tert.butyl-2-imino-imidazolidine hydrochloride in caustic soda and 35.8 g of p-[2-(o-chloro-benzamido)-ethyl]-benzenesulfonyl chloride l- The [p-[2-(o-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine with m.p. 152 - 154° (from ethanol).

EKSEMPEL 4 EXAMPLE 4

a) Analogt eksempel la) oppnår man fra 17,8 g l-butyl-2-imino-imidazolidin-hydroklorid i natronlut og 35,4 g p-[2-(o-metoksy-benzamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(o-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazo1idinet med smp. 145 - 146° (fra metanol). a) Analogous example la) is obtained from 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride in caustic soda and 35.4 g of p-[2-(o-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride The 1-[p-[2-(o-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazo1idine with m.p. 145 - 146° (from methanol).

Det som utgangsstoff anvendte sulfonylklorid fremstilles som folger: b) Analogt eksempel 2b-d) oppnår man ved å gå ut fra 17,1 g o-metoksy-benzoylklorid med 20,3 g p-nitro-fenetylamin N-(p-nitro-fenetyl)-o-metoksy-benzamidet med smp. 149 - 150° (fra eddiksyreetylester); 30,0 g av denne nitroforbindelse reduseres med 16,0 g jernpulver til N-(p-amino-fenetyl)-o-metoksy-benz-amid-hydrokloridet med smp. 211 - 214° (fra metanol), fra hvilket 30,5 g diazoteres i konsentrert saltsyre med 7,6 g natriumnitrit; diazoniumsaltopplosningen gir med en opplosning av cupriklorid i vann og iseddik, hvilken er mettet med svoveldioksyd, p-[2-(o-metoksy-benzamido)-etyl]-benzensulfonyl-kloridet, hvilket smelter ved 140 - 143° (råprodukt). The sulfonyl chloride used as starting material is prepared as follows: b) Analogous to example 2b-d) is obtained by starting from 17.1 g of o-methoxy-benzoyl chloride with 20.3 g of p-nitro-phenethylamine N-(p-nitro- phenethyl)-o-methoxy-benzamide with m.p. 149 - 150° (from acetic acid ethyl ester); 30.0 g of this nitro compound is reduced with 16.0 g of iron powder to the N-(p-amino-phenethyl)-o-methoxy-benz-amide hydrochloride with m.p. 211 - 214° (from methanol), from which 30.5 g is diazotized in concentrated hydrochloric acid with 7.6 g of sodium nitrite; the diazonium salt solution gives with a solution of cupric chloride in water and glacial acetic acid, which is saturated with sulfur dioxide, the p-[2-(o-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride, which melts at 140 - 143° (crude product).

EKSEMPEL 5 EXAMPLE 5

a) Analogt eksempel la) oppnår man fra 16,4 g l-propyl-2-imino-imidazolidin-hydroklorid i natronlut og 35,4 g p-[2-(m-metoksy-benzamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(m-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-propy1-imidazolidinet med smp. 144 - 147° (fra eddiksyre-etylester). a) Analogous example la) is obtained from 16.4 g of 1-propyl-2-imino-imidazolidine hydrochloride in caustic soda and 35.4 g of p-[2-(m-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride The 1-[p-[2-(m-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-propyl-imidazolidine with m.p. 144 - 147° (from acetic acid ethyl ester).

Det som utgangsstoff anvendte sulfonylklorid fremstilles som folger: b) Analogt eksempel 2b-d) oppnår man ved å gå ut fra 17,1 g m-metoksy-benzoylklorid med 20,3 g p-nitro-fenetylamin N-(p-nitro-fenetyl)-m-metoksy-benzamidet med smp. 151 - 152° (fra eddiksyreetylester); 30,0 g av denne nitroforbindelse reduseres med 16,0 g jernpulver til N-(p-amino-fenetyl)-m-metoksy-benzamid-hydrokloridet med smp. 205 - 209°, fra hvilket 30,5 g diazoteres i konsentrert saltsyre med 7,6 g natriumnitrit; diazo-niumsaltopplbsningen gir med en opplbsning av cupriklorid i vann og iseddik, hvilken er mettet med svoveldioksyd, p-[2-(m-metoksy-benzamido)-etyl]-benzensulfonyl-kloridet (råprodukt). The sulfonyl chloride used as starting material is prepared as follows: b) Analogous to example 2b-d) is obtained by starting from 17.1 g of m-methoxy-benzoyl chloride with 20.3 g of p-nitro-phenethylamine N-(p-nitro- phenethyl)-m-methoxy-benzamide with m.p. 151 - 152° (from acetic acid ethyl ester); 30.0 g of this nitro compound is reduced with 16.0 g of iron powder to the N-(p-amino-phenethyl)-m-methoxy-benzamide hydrochloride with m.p. 205 - 209°, from which 30.5 g is diazotized in concentrated hydrochloric acid with 7.6 g of sodium nitrite; The diazonium salt solution gives, with a solution of cupric chloride in water and glacial acetic acid, which is saturated with sulfur dioxide, p-[2-(m-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride (crude product).

EKSEMPEL 6 EXAMPLE 6

Analogt eksempel la) oppnår man fra 17,8 g l-butyl-2-imino-imidazolidin-hydroklorid i natronlut og 35,4 g p-[2-(m-metoksy-benzamido)-etyl]-benzensu lfonyl-klorid l-[p-[2-( m-metok s y-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet med smp. 137 - 141° (fra metanol). Analogous to example la) is obtained from 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride in caustic soda and 35.4 g of p-[2-(m-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride l -[p-[2-( m-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine with m.p. 137 - 141° (from methanol).

EKSEMPEL 7 EXAMPLE 7

Analogt eksempel la) oppnår man fra 17,8 g 1-tert.butyl-2-imino-imidazolidin-hydroklorid i natronlut og 35,4 g p-[2-(m-metoksy-benzamido)-etyl]-benzensulfonyl-klorid l-[ p-[2-(rn-metoksy-benzamido^etylJ-fenylsulfonylJ^-imino-S-tert.butyl-imidazolidinet med smp. 134 - 136° (fra eddiksyreetylester). Analogous to example la) is obtained from 17.8 g of 1-tert.butyl-2-imino-imidazolidine hydrochloride in caustic soda and 35.4 g of p-[2-(m-methoxy-benzamido)-ethyl]-benzenesulfonyl chloride The l-[p-[2-(rn-methoxy-benzamido^ethyl J-phenylsulfonyl J^-imino-S-tert.butyl-imidazolidine with m.p. 134 - 136° (from acetic acid ethyl ester).

EKSEMPEL 8 EXAMPLE 8

a) Analogt eksempel la) oppnår man fra 17,8 g 1-tert.butyl-2-imino-imidazolidin-hydroklorid i natronlut og 33,8 g p-[2-(o-to1uamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(o-toluamido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet med smp. 160 - 161°. a) Analogous to example la) is obtained from 17.8 g of 1-tert.butyl-2-imino-imidazolidine hydrochloride in caustic soda and 33.8 g of p-[2-(o-to1uamido)-ethyl]-benzenesulfonyl chloride The l-[p-[2-(o-toluamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine with m.p. 160 - 161°.

Det som utgangsstoff anvendte sulfonylklorid fremstilles som folger: b) Analogt eksempel 2b-d) oppnår man ved å gå ut fra 15,5 g o-toluoylklorid med 20,3 g p-nitro-fenetylamin N-(p-nitro-fenetyl )-p-toluamidet (råprodukt); 28,4 g av denne nitroforbindelse reduseres med 16,0 g jernpulver til N-(p-amino-fenetyl)-o-toluamid-hydrokloridet (råprodukt), av hvilket 28,4 g diazoteres i konsentrert saltsyre med 7,6 g natriumnitrit; diazoniumsalt-ppplosningen gir med en opplosning av cupriklorid i vann og iseddik, hvilken er mettet med svoveldioksyd, p-[2-(o-toluamido)-etyl]-benzensulfonyl-kloridet (råprodukt). The sulfonyl chloride used as starting material is prepared as follows: b) Analogous to example 2b-d) is obtained by starting from 15.5 g of o-toluoyl chloride with 20.3 g of p-nitro-phenethylamine N-(p-nitro-phenethyl) -p-toluamide (crude product); 28.4 g of this nitro compound is reduced with 16.0 g of iron powder to the N-(p-amino-phenethyl)-o-toluamide hydrochloride (crude product), of which 28.4 g is diazotized in concentrated hydrochloric acid with 7.6 g of sodium nitrite ; the diazonium salt p solution gives with a solution of cupric chloride in water and glacial acetic acid, which is saturated with sulfur dioxide, the p-[2-(o-toluamido)-ethyl]-benzenesulfonyl chloride (crude product).

EKSEMPEL 9 EXAMPLE 9

a) Analogt eksempel la) oppnår man fra 13,6 g l-metyl-2-imino-imidazolidin-hydroklorid i natronlut og 39,0 g p-[2-(2-metoksy-5-klor-benzamido)- etyl]-benzensulfonyl-klorid l-[ p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-metyl-imidazolidinet med smp. 140 - 141° (fra eddikester). a) Analogous example la) is obtained from 13.6 g of 1-methyl-2-imino-imidazolidine hydrochloride in caustic soda and 39.0 g of p-[2-(2-methoxy-5-chloro-benzamido)-ethyl] -benzenesulfonyl chloride 1-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-methyl-imidazolidine with m.p. 140 - 141° (from vinegar).

Det som utgangsstoff anvendte sulfonylklorid fremstilles som folger: b) Analogt eksempel 2b-d) oppnår man ved å gå ut fra 20,6 g 2-metoksy-b-klor-benzoylklorid med 20,3 g p-nitro-fenetylamin N-(p-nitro-fenetyl)-2-metoksy-5-klor-benzamidet med smp. 158 - 160°; 30,0 g av denne nitroforbindelse reduseres med 16,0 g jernpulver til N-(p-amino-fenetyl)-2-metoksy-5-klor-benzamid-hydrokloridet (råprodukt), av hvilket 34,0 g diazoteres i konsentrert saltsyre med 7,6 g natriumnitrit; diazoniumsaltopplosningen gir med en opplosning av cupriklorid i vann og iseddik, hvilken er mettet med svoveldioksyd, p-[2-(2-metoksy-5-klor-benzamido)-etyl]-benzensulfonyl-kloridet (råprodukt). The sulfonyl chloride used as starting material is prepared as follows: b) Analogous to example 2b-d) is obtained by starting from 20.6 g of 2-methoxy-b-chloro-benzoyl chloride with 20.3 g of p-nitro-phenethylamine N-( The p-nitro-phenethyl)-2-methoxy-5-chloro-benzamide with m.p. 158 - 160°; 30.0 g of this nitro compound is reduced with 16.0 g of iron powder to the N-(p-amino-phenethyl)-2-methoxy-5-chloro-benzamide hydrochloride (crude product), of which 34.0 g is diazotized in concentrated hydrochloric acid with 7.6 g of sodium nitrite; the diazonium salt solution gives with a solution of cupric chloride in water and glacial acetic acid, which is saturated with sulfur dioxide, the p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-benzenesulfonyl chloride (crude product).

EKSEMPEL 10 EXAMPLE 10

Analogt eksempel la) oppnår man fra 17,8 g l-butyl-2-imino-imidazolidin-hydroklorid i natronlut og 39,0 g p-[2-(2-metoksy-5-klor-benzamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet med smp. 94 - 97° (fra eddiksyreetylester). Analogous example la) is obtained from 17.8 g of 1-butyl-2-imino-imidazolidine hydrochloride in caustic soda and 39.0 g of p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-benzenesulfonyl -chloride 1-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine with m.p. 94 - 97° (from acetic acid ethyl ester).

EKSEMPEL 11 EXAMPLE 11

Analogt eksempel la) oppnår man fra 17,8 g 1-tert.butyl-2-imino-imidazolidin-hydroklorid i natronlut og 39,0 g p-[2-(2-metoksy-5-klor-benzamido)-etyl]-benzensulfonyl-klorid l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet med smp. 120 - 122 . Analogously to example la) one obtains from 17.8 g of 1-tert.butyl-2-imino-imidazolidine hydrochloride in caustic soda and 39.0 g of p-[2-(2-methoxy-5-chloro-benzamido)-ethyl] -benzenesulfonyl chloride 1-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine with m.p. 120 - 122 .

Sluttproduktet renses ved elusjonskromatografi på silikagel med kloroform-etanol (9:1) som elusjonsmiddel. Fra de forste fraksjoner vinner man tilbake uforandret utgangsprodukt, fra de siste fraksjoner sluttproduktet. The final product is purified by elution chromatography on silica gel with chloroform-ethanol (9:1) as eluent. From the first fractions you get back unchanged starting product, from the last fractions the final product.

EKSEMPEL 12 EXAMPLE 12

Analogt eksempel la) oppnår man fra 20,4 g l-cykloheksyl-2-imino-imidazolidin-hydroklorid i natronlut og 39,0 g p-[2-(2-metok sy-5-k lor-benzamido)-et yl]- benzensulfonyl-klorid lrL~ P_[ 2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet med smp. 167 - 170° (fra metanol). Analogous to example la) is obtained from 20.4 g of 1-cyclohexyl-2-imino-imidazolidine hydrochloride in caustic soda and 39.0 g of p-[2-(2-methoxy-5-chloro-benzamido)-ethyl ]-benzenesulfonyl chloride lrL~ P_[ 2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine with m.p. 167 - 170° (from methanol).

EKSEMPEL 13 EXAMPLE 13

Analogt eksempel la) oppnår man fra 17,8 g 1-tert.butyl-2-imino-imidazolidin-hydroklorid i natronlut og 41,4 g p-[2-(3,4,5-trimetoksy-benzamido)- etyl]-benzensulfonyl-klorid l-[p-[2-(3,4, 5-trimetoksy-benzamido)- etyl]-fenylsulfonyl]-2-imino-3-tert. butyl-imidazolidinet med smp. 130 - 132° (fra eddiksyreetylester-eter). Analogously to example la) one obtains from 17.8 g of 1-tert.butyl-2-imino-imidazolidine hydrochloride in caustic soda and 41.4 g of p-[2-(3,4,5-trimethoxy-benzamido)-ethyl] -benzenesulfonyl chloride 1-[p-[2-(3,4,5-trimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert. the butyl-imidazolidine with m.p. 130 - 132° (from acetic acid ethyl ester ether).

Det som utgangsprodukt anvendte sulfonylklorid fremstilles analogt eksempel 9b). The sulfonyl chloride used as starting product is prepared analogously to example 9b).

EKSEMPEL 14 EXAMPLE 14

Analogt eksempel la) oppnår man fra 17v8 g 1-tert.butyl-2-imino-imidazolidin-hydroklorid i natronlut og 28,9 g p-(2-butyryl-amido-etyl)-benzensulfonyl-klorid l-[p-(2-butyrylamido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet med smp. Analogously to example la) one obtains from 17v8 g of 1-tert.butyl-2-imino-imidazolidine hydrochloride in caustic soda and 28.9 g of p-(2-butyryl-amido-ethyl)-benzenesulfonyl chloride l-[p-( The 2-butyrylamido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine with m.p.

148 - 149° (fra eddiksyreetylester). 148 - 149° (from acetic acid ethyl ester).

EKSEMPEL 15 EXAMPLE 15

a) 38,1 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen a) 38.1 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base

frisettes med 300 ml 2-n natronlut. Den ekstraheres med metyl- free with 300 ml 2-n caustic soda. It is extracted with methyl

enklorid. Den med natriumsulfat torkede metylenkloridopplosning tilsettes 50,5 g trietylamin. Derpå tildrypper man ved værelsetemperatur oppløsningen av 9,3 g propionsyreklorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at oppløsningen rores i 1 time ved værelsetemperatur, vasker man den med 100' ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter torking med natriumsulfat, filtrering og inndampning l-[p-(2-propionamido-etyl)-fenylsulfo 2-imino-3-n-propyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 127 - 129°. monochloride. 50.5 g of triethylamine is added to the methylene chloride solution dried with sodium sulfate. The solution of 9.3 g of propionic acid chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution is stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after drying with sodium sulfate, filtration and evaporation 1-[p-(2-propionamido-ethyl)-phenylsulfo 2-imino-3-n-propyl-imidazolidine, which recrystallized from acetic ester melts at 127 - 129° .

På analog måte oppnår man fra 38,1 g l-[p-(2-amino-etyl)-fenyl-sulf onyl]-2-imino-3-n-propyl-imidazolidin-dihydroklorid og: 9,3 g propionyl-klorid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet <*> 1/6 E^O, smp. 130 - 134°; 10,7 g n-butyrylklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet • H^O, smp. 114 - 116°; 12,1 g n-valeroylklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, smp. 130 - 132°; 12,1 g isovaleriansyreklorid l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, smp. 135-136°; 10,5 g cyklopropankarboksylsyreklorid l-[p-(2-cyklopropankar-boksamido-etyl)- f enylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, smp. 142 - 143°•, 14,7 g cykloheksylkarboksylsyreklorid l-[p-(2-cykloheksylkarbok-samido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, smp. 144 - 146°; 15,5 g o-toluoylklorid l-[p-[2-(2-tolu-metylamido)-etyl]-fenyl-sulf onyl] -2- imino-3-n-propyl-imidazol idinet , smp. 114 '- 116°; 17,5 g o-klorbenzoylklorid 1-[p-[2-( 2-klorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, smp. 145 - 146°; 21,9 g o-brombenzoylklorid l-[p-[2-(2-brombenzamido)-etyl]-f enylsulforiyl]-2-imino-3-n-propyl-im.idazolidinet,. smp. 137 - 138°; 16,9 g 2,5-dimetylbenzoylklorid l-[p-[2-(2,5-dimetylbenzamido)-etyl]- fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, smp. 117 - 118°; 14,1 g a-klorsmorsyreklorid l-[p-(2-a-klorbutyramido-etyl)-f enylsulf on-yl]-2-imino-3-n-propyl-imidazolidinet, smp. 123 - 124°; • . ■ 17,0 g m-metoksy-benzoylklorid l-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulf onyl]-2--imino-3-propyl-imidazolidinet, smp. 144 - 147°; 10,5 g 1-met-akryloylklorid l-[ p-[ 2-(1-met-akryrylamidc)-etyl]-f enylsulf onyl]-2-imino-3-propyl-imidazoIidinet, smp. 139-140°; 21,0 g 2,4-diklorbenzoylklorid l-[p-[2-(2,4-diklorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-propyl-imidazolidinet, smp. 122 - 124°.; b) Utgangsmaterialet l-[p-(2-amino-etyl)-fenyl-sulfonyl]-2-imino-3-propyl-imidazolidin-dihydroklorid. oppnås etter to frem-gangsmåter: 1) 35,2 g l-[pr(2-acetamino-etyI)-fenylsulfonyl]-2-imino-3-propyl-imidazolidin opplbses i; 370 ml 2-n saltsyre, og oppl<y>sningen kokes i 6 timer ved tilbakelop. Oppløsningen inndampes så i vakuum til tbrrhet,-og den erholdte olje opplbses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-benzen-sulf onyl] -2- imino-3-propyl- imidazol id in-dihydrok lorid et med smp. 255 - 256°.. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-fenylsulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, In an analogous manner, one obtains from 38.1 g of 1-[p-(2-amino-ethyl)-phenyl-sulfonyl]-2-imino-3-n-propyl-imidazolidine dihydrochloride and: 9.3 g of propionyl- chloride 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine <*> 1/6 E^O, m.p. 130 - 134°; 10.7 g of n-butyryl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine • H 2 O, m.p. 114 - 116°; 12.1 g of n-valeroyl chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 130 - 132°; 12.1 g of isovaleric acid chloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 135-136°; 10.5 g cyclopropanecarboxylic acid chloride 1-[p-(2-cyclopropanecarboxamido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 142 - 143°•, 14.7 g of cyclohexylcarboxylic acid chloride 1-[p-(2-cyclohexylcarboxy-samido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 144 - 146°; 15.5 g of o-toluoyl chloride 1-[p-[2-(2-tolu-methylamido)-ethyl]-phenyl-sulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 114' - 116°; 17.5 g o-chlorobenzoyl chloride 1-[p-[2-(2-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 145 - 146°; 21.9 g of o-bromobenzoyl chloride 1-[p-[2-(2-bromobenzamido)-ethyl]-phenylsulforiyl]-2-imino-3-n-propyl-imidazolidine,. m.p. 137 - 138°; 16.9 g of 2,5-dimethylbenzoyl chloride 1-[p-[2-(2,5-dimethylbenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, m.p. 117 - 118°; 14.1 g of α-chlorobutyric acid chloride 1-[p-(2-α-chlorobutyramido-ethyl)-phenylsulfon-yl]-2-imino-3-n-propyl-imidazolidine, m.p. 123 - 124°; • . ■ 17.0 g of m-methoxy-benzoyl chloride 1-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2--imino-3-propyl-imidazolidine, m.p. 144 - 147°; 10.5 g of 1-meth-acryloyl chloride 1-[p-[2-(1-meth-acrylamidec)-ethyl]-phenylsulfonyl]-2-imino-3-propyl-imidazoylidine, m.p. 139-140°; 21.0 g of 2,4-dichlorobenzoyl chloride 1-[p-[2-(2,4-dichlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-propyl-imidazolidine, m.p. 122 - 124°.; b) The starting material 1-[p-(2-amino-ethyl)-phenyl-sulfonyl]-2-imino-3-propyl-imidazolidine dihydrochloride. is obtained by two methods: 1) 35.2 g of 1-[pr(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-propyl-imidazolidine is dissolved in; 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux. The solution is then evaporated in a vacuum to dryness, and the resulting oil is dissolved in alcohol. In the cold, 1-[p-(2-amino-ethyl)-benzene-sulfonyl]-2-imino-3-propyl-imidazolidine-dihydrochloride is crystallized with m.p. 255 - 256°.. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-phenylsulfonamide hydrochloride [lit.: E. Miller et al., J. Am. Chem. Soc. 62, 2101,

(1940)] og 16 g N-(2-klor-etyl)-N-propyl-cyanamid oppvarmes under roring i 1 time i oljebad på 110°. Etter avkjoling heller, man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erhold<+>e olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-propyl-imidazolidin-dihydrokloridet med smp. 255 - 256°. (1940)] and 16 g of N-(2-chloro-ethyl)-N-propyl-cyanamide are heated with stirring for 1 hour in an oil bath at 110°. After cooling down rather, one on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. On cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-propyl-imidazolidine dihydrochloride is precipitated with m.p. 255 - 256°.

EKSEMPEL 16 EXAMPLE 16

38,1 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin-dihydroklorid opploses i 200 ml vann og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylen-klorid. Den med natriumsulfat torkede metyl enklorid-opplosning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur oppløsningen av 7,9 g acetylklorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at oppløsningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir- etter tdrking med-natriumsulfat, filtrering og inndampning l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 133 - 135°. 38.1 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine dihydrochloride are dissolved in 200 ml of water and the base is liberated with 300 ml of 2-n sodium hydroxide solution. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 7.9 g of acetyl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give, after drying with sodium sulfate, filtration and evaporation 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine, which recrystallized from acetic ester melts at 133 - 135°.

EKSEMPEL 17 EXAMPLE 17

38,1 g l-[ p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylen-klorid. Den med natriumsulfat torkede metylenkloridopplosning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur oppldsningen av 9,3 g propionsyreklorid i 100 ml metylenklorid i lopet av. 20 minutter. Etter--at oppløsningen er 38.1 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base is liberated with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the methylene chloride solution dried with sodium sulphate. The solution of 9.3 g of propionic acid chloride in 100 ml of methylene chloride is then added dropwise at room temperature. 20 minutes. After--that the resolution is

rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser, ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter tdrking med natriumsulfat, filtrering og inndampning l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 111 - 112°.• stirred for 1 hour at room temperature, it is washed with 100 ml of 2N caustic soda and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after drying with sodium sulfate, filtration and evaporation 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine, which recrystallized from acetic ester melts at 111 - 112° .•

EKSEMPEL 18 EXAMPLE 18

a) 38,1 g l-[p-(2-amino-etyl)-f enylsulf onyl]-2-imi"no-3-isopro-pyl-imidazolidin-dihydroklorid opploses i 200 ml varm, og basen a) 38.1 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine dihydrochloride are dissolved in 200 ml hot, and the base

frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenkloridopplosning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur opplo-sningen av 10,7 g smorsyreklorid i 100- ml metylenklorid i lopet av 20 minutter. Etter at oppløsningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2- n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med.raetylenklorid. De forente metylenklorid-faser gir etter tdrking med natriumsulfat, filtrering 'og inndampning l-[ p- ( 2-butyramido-etyl j_-f enylsulf onyl ] -2- imi no-3- isopropyl-imidazolidin, som omkrystallisert fra; eddikester smelter ved 139 - 140°. free with 300 ml 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the methylene chloride solution dried with sodium sulfate. The solution of 10.7 g of butyric acid chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2N caustic soda and twice with 100 ml of water. The aqueous phases are extracted twice with ethylene chloride. The combined methylene chloride phases give after drying with sodium sulfate, filtration and evaporation 1-[p-(2-butyramido-ethyl j_-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine, which is recrystallized from; acetic ester melts at 139 - 140°.

På analog måte oppnår man fra 38,1 g l-[p-(2-amino-etyl)-f eny1suIfon yl]-2-imino-3-isopropyl-imidazolidin-dihydroKlorid og: 10,7 g butyrylklorid 1-fp-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imi-dazolidinet, smp. 13-9 - 140°; In an analogous manner, one obtains from 38.1 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine-dihydrochloride and: 10.7 g of butyryl chloride 1-fp- (2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine, m.p. 13-9 - 140°;

12,1 g n-valeriansyreklorid l-[p-(2-valeramido-etyl)-fenylsulfo-nyl] -2- imino-3-isopropyl-imidazoli.dinet , smp. 123 - 124°; 12.1 g n-valeric acid chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, m.p. 123 - 124°;

10,5 g cyklopropankarboksylsyreklorid l-[p-(2-cyklopropankar-boksamido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazol1-dinet, smp. 114 - 116°; 10.5 g of cyclopropanecarboxylic acid chloride 1-[p-(2-cyclopropanecarboxamido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazole-1-dine, m.p. 114 - 116°;

15 ,5 g p-tdluoylklorid.l-Cp-[2-(2-toluamido-etylJ-fenylsulfonyl]- 15.5 g p-trifluoroyl chloride.1-Cp-[2-(2-toluamido-ethyl J-phenylsulfonyl]-

2-imino-3-isopropyl-imidazolidinet, smp. 132 - 134°; The 2-imino-3-isopropyl-imidazolidine, m.p. 132 - 134°;

17,5 g o-klorbenzoylklorid l-[p-[2-(2-klorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, smp. 132 - 134°; 17.5 g of o-chlorobenzoyl chloride 1-[p-[2-(2-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine, m.p. 132 - 134°;

10,5 g 1-metakryloylklorid l-[p-[2-(1-metakryl-amido)-etyl]-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet • 1 F^O, 10.5 g of 1-methacryloyl chloride 1-[p-[2-(1-methacrylamido)-ethyl]-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine • 1 F^O,

smp. 106 - 107°. m.p. 106 - 107°.

b) Utgangsmaterialet l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin-dihydroklorid oppnås etter to b) The starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine dihydrochloride is obtained after two

fremgangsmåter: procedures:

1) 35,2 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opp-løsningen kokes i 6 timer ved tilbakelop. Oppløsningen inndampes så i vakuum til tørrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-fenyl-su lfonyl]- 2-imino-3-isopropyl-imidazolidin-dihydrokloridet med smp. 249 - 250°. 2) En bland ing av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-fenylsulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, 1) 35.2 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine are dissolved in 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux . The solution is then evaporated in vacuo to dryness, and the resulting oil is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-phenyl-sulfonyl]-2-imino-3-isopropyl-imidazolidine dihydrochloride is crystallized with m.p. 249 - 250°. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-phenylsulfonamide hydrochloride [lit.: E. Miller et al., J.am.chem .Soc. 62, 2101,

(1940)] og 16 g N-(2-klor-etyl)-N-isopropyl-cyanamid oppvarmes under rdring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opplbses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidin-dihydrokloridet med smp. 249 - 250°• (1940)] and 16 g of N-(2-chloro-ethyl)-N-isopropyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. On cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine dihydrochloride is precipitated with m.p. 249 - 250°•

EKSEMPEL 19 EXAMPLE 19

a) 39,7 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenklorid-opplosning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur oppløsningen av 7,9 g acetylklorid i 100 ml metylenklorid i lopet av. 20 minutter. Etter at oppløsningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. Dé vandige faser ekstraherer man to ganger med metylenklorid. De forente metylen-klorid-f aser gir etter tdrking med natriumsulfat, filtrering og inndampning l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 130 - 131°.- a) 39.7 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base is liberated with 300 ml of 2-n sodium hydroxide solution. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 7.9 g of acetyl chloride in 100 ml of methylene chloride is then added dropwise at room temperature. 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after drying with sodium sulfate, filtration and evaporation 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, which recrystallized from acetic ester melts at 130 - 131°.-

På analog måte oppnår man frå 39,7 g l-[p-(2-amino-etyl)-f enylsulfonyl]-2-imino-3-butyl-imidazolidin-dihydroklorid og: 10,7 g butyrylklorid 1-|[ p- (2-butyramido-etyl) -f enylsulf onyl]-2-imino-3-butyl-imidazolidinet, smp. 123 — 124°;-13,0 g 2-metyl-butyryiklorid l-[p-[2-( 2-metyl-butyramido)--etyl]-fenylsulfonyl]-2-imino-3^butyl-imidazolidinet, smp. 114 - 116°; 13,0 g valeriansyreklorid l-[p-(2-valeramido-etyl)-fenylsulfo-nyl]-2-imino-3-butyl-imidazolidinet, smp. 130°; 13,0 g isovaleriansyreklorid l-[-p-(2-isovaleramido-etyl)-fenyl-su lfonyl]-2 -imino-3-butyl-imidazolidinet, smp. 130 - 130,5 ; 14,5 g caproylklorid L-[p-(2-capronamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 129 - 130°; 17,5 g caprylsyreklorid l-[p-( 2-oktanamido-et.yl)-f enylsulf onyl]-2-imino-3-butyl-imidazoIidinet, smp..130 - 13.1°;. 18,9 g o-klor-benzoylklorid l-[p-[2-(2-klorbenzamido)-etyl]-f enyls.ulfonyl]-2-iminQ-3-n^butyl-imidazolidinet, smp. 155 - 157°; 17,1 g o-metoksybenzoylklorid l-[p-[2-(2-metoksybenzamido)-etyl]-f enylsulf onyl]-2-imi'no-3-butyl-imidazolidinet, smp. 145 - 146° •, 18,8 g p-klorfenyl-acetylklorid l-[p-(2-[2-(4-klorfenyl)-acetamido]-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 163 - 164°; 19,7 g 2-fenyl-butyrylklorid l-[ p-f_2-( 2-f enyl-butyramido) - etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 127 - 128°; 12,5 g-1-etyl-propionylklorid l-[p-[2-(1-etyl-propionamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 125 - 126°; 9,2 g akryloylklorid l-[p-(2-akrylamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 153 - 154°; 22,1 g 2-metoksy-5-klor-benzoylklorid l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-f enylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 94 - 97°; 18,0 g 3-metoksy-benzoylklorid l-[p-[2-(3-metoksy-berizamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 139 - 141°; 16 ,5 g l-metyl-3-cykloheksen-karboksylsyreklorid l-[p-[2-(l-metyl-3-cykloheksenkårboksamido)-etyl]-f enylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 149 - 150°; 21,0 g 3,4-dimetoksy-benzoylklorid l-[p-[2-(3,4-dimetoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 169 - 170°; b) Utgangsmaterialet l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin-dihydroklorid oppnås etter to fremgangsmåter: 1) 36,65 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inndampes så i vakuum, til torrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-fenylsulfo-nyl]-2-imino-3-butyl-imidazolidin-dihydrokloridet med smp. 231 - 233°. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-benzensulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, In an analogous manner, one obtains from 39.7 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride and: 10.7 g of butyryl chloride 1-|[ p - (2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 123 — 124°;-13.0 g of 2-methyl-butyryl chloride 1-[p-[2-(2-methyl-butyramido)--ethyl]-phenylsulfonyl]-2-imino-3^butyl-imidazolidine, m.p. 114 - 116°; 13.0 g valeric acid chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 130°; 13.0 g of isovaleric acid chloride 1-[-p-(2-isovaleramido-ethyl)-phenyl-sulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 130 - 130.5; 14.5 g caproyl chloride L-[p-(2-capronamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 129 - 130°; 17.5 g of caprylic acid chloride 1-[p-(2-octanamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazoIidine, m.p. 130 - 13.1°;. 18.9 g of o-chloro-benzoyl chloride 1-[p-[2-(2-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-iminQ-3-n-butyl-imidazolidine, m.p. 155 - 157°; 17.1 g of o-methoxybenzoyl chloride 1-[p-[2-(2-methoxybenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 145 - 146° •, 18.8 g p-chlorophenyl-acetyl chloride 1-[p-(2-[2-(4-chlorophenyl)-acetamido]-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine , m.p. 163 - 164°; 19.7 g of 2-phenyl-butyryl chloride 1-[p-f_2-(2-phenyl-butyramido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 127 - 128°; 12.5 g of 1-ethyl-propionyl chloride 1-[p-[2-(1-ethyl-propionamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 125 - 126°; 9.2 g of acryloyl chloride 1-[p-(2-acrylamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 153 - 154°; 22.1 g of 2-methoxy-5-chloro-benzoyl chloride 1-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 94 - 97°; 18.0 g of 3-methoxy-benzoyl chloride 1-[p-[2-(3-methoxy-berizamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 139 - 141°; 16.5 g of 1-methyl-3-cyclohexene carboxylic acid chloride 1-[p-[2-(1-methyl-3-cyclohexenecarboxamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 149 - 150°; 21.0 g of 3,4-dimethoxy-benzoyl chloride 1-[p-[2-(3,4-dimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 169 - 170°; b) The starting material l-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride is obtained by two methods: 1) 36.65 g of l-[p-(2-acetamino -ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine is dissolved in 370 ml of 2-n hydrochloric acid, and the solution is refluxed for 6 hours. The solution is then evaporated in vacuo to dryness, and the resulting oil is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride is crystallized with m.p. 231 - 233°. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-benzenesulfonamide hydrochloride [lit.: E. Miller et al., J.am.chem. Soc. 62, 2101,

(1940)] og 16 g N-( 2-klor-etyl ).-N-butyl-cyanamid oppvarmes under roring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid^. de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol, og innstilles, sur med.mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin-dihydrokloridet med smp. 231 - 233°. (1940)] and 16 g of N-(2-chloro-ethyl).-N-butyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The clear solution obtained is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride^. the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and set, acidified with saturated alcoholic hydrochloric acid. On cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride is precipitated with m.p. 231 - 233°.

EKSEMPEL. 20 EXAMPLE. 20

41,5 g 1-Qp-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid-monohydrat opploses i 200 ml vann, og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenkloridopp-ldsning tilsettes 50,5 g trietylamin. t Deretter tildrypper man ved værelsetemperatur opplosningen av 10 g propionsyre-klorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenkloridfaser gir etter torking med natriumsulfat, filtrering og- inndampning- l-[p-(2-propionamido-etyl)-fenylsulfo-nyl]-2-imino-3-isobutyl-imidazolidin, som. omkrystallisert fra eddikester smelter, ved 140 - 142°. 41.5 g of 1-Qp-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride monohydrate is dissolved in 200 ml of water, and the base is freed with 300 ml of 2-N caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. t Then, at room temperature, the solution of 10 g of propionic acid chloride in 100 ml of methylene chloride is added dropwise over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases, after drying with sodium sulfate, filtration and evaporation, give 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, which recrystallized from acetic ester melts, at 140 - 142°.

På analog måte oppnår man fra 41,5 g l-[p-(2-amino-etyl)-f enylsulfonyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid-monohydrat og: 11,7 g smorsyreklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 138 - 139°; In an analogous manner, one obtains from 41.5 g of l-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride monohydrate and: 11.7 g of butyric acid chloride l-[ p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 138 - 139°;

13,0 g valeriansyreklorid l-[p-(2-valeramido-etyl)-fenylsulfo-nyl]-2-imino-3-isobutyl-imidazolidinet, smp. 137 - 140°; 13.0 g valeric acid chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 137 - 140°;

13,0 g isovaleriansyreklorid l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 150 - 152°; 13.0 g of isovaleric acid chloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 150 - 152°;

13,0 g pivaloylklorid l-[p-(2-pivalamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 165 - 167°; 13.0 g of pivaloyl chloride 1-[p-(2-pivalamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 165 - 167°;

14.4 g heksanoylklorid l-[p-(2-heksanamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 139 - 140°; 14.4 g of hexanoyl chloride 1-[p-(2-hexanamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 139 - 140°;

10.5 g cyklopropan-karboksylsyreklorid l-[p-(2-cyklopropan-k årboksamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 163 - 164°; 10.5 g cyclopropane carboxylic acid chloride 1-[p-(2-cyclopropane-carboxamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 163 - 164°;

15.6 g cykloheksan-karboksylsyreklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-f enyl-sulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 175 - 177°; 15.6 g cyclohexane-carboxylic acid chloride 1-[p-(2-cyclohexane-carboxamido-ethyl)-phenyl-sulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 175 - 177°;

16.7 g o-toluoylklorid l-[p-(2-toluamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 138 - 140°; 16.7 g of o-toluoyl chloride 1-[p-(2-toluamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 138 - 140°;

18,4 g o-metoksy-benzoylklorid 1-[p-[2-(2-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 110 - 111°; 18.4 g of o-methoxy-benzoyl chloride 1-[p-[2-(2-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 110 - 111°;

22,3 g 2-metoksy-5-klor-benzoylklorid l-[p-[2-(metoksy-5-klor-benzamido ) -etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 117 - 119°; 22.3 g of 2-methoxy-5-chloro-benzoyl chloride 1-[p-[2-(methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 117 - 119°;

18.3 g 3,4-dimetyl-benzoylklorid l-[p-[2-(3,4-dimetyl-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 158,5 - 160°; 18.3 g of 3,4-dimethyl-benzoyl chloride 1-[p-[2-(3,4-dimethyl-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 158.5 - 160°;

23,7 g o-brom-benzoylklorid l-[ p-[ 2-( 2-br'ombenzamido) - etyl] - fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 158 - 160°; 23.7 g o-bromo-benzoyl chloride 1-[p-[2-(2-brombenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 158 - 160°;

20.4 g p-klorfenyl-acetylklorid l-[p-[2-(4-klorfenyl-acetamido)-etyl]-f enylsulfonylj-2-imino-3-isobutyl-imidazolidinet, smp. 20.4 g of p-chlorophenyl-acetyl chloride 1-[p-[2-(4-chlorophenyl-acetamido)-ethyl]-phenylsulfonyl l-2-imino-3-isobutyl-imidazolidine, m.p.

175 - 176°; 175 - 176°;

22,4 g 2,4-diklor-benzoylklorid !"-[ p-[2-( 2 ,4-dik lor-benzamido )-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 102,5 - 104°; 22.4 g of 2,4-dichloro-benzoyl chloride!"-[p-[2-(2,4-dichloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 102 .5 - 104°;

10,2 g acetanhydrid l-[ p- ( 2-acetamido-etyl )-f enylsulf onyl]-2-imino-3-isobutyl-imidazolidinet, smp. 149 - 151°. 10.2 g of acetic anhydride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 149 - 151°.

a) Utgangsmaterialet l-[ p-( 2-amino-etyl ).-f enylsulf onyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid-monohydrat oppnås a) The starting material 1-[p-(2-amino-ethyl).-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride monohydrate is obtained

etter to fremgangsmåter: by two methods:

1) 36,65 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin opploses i 370 ml 2-ri saltsyre, og opplosningen kokes i 6 timer under tilbakeldp. Opplosningen inndampes så i vakuum til tdrrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-benzensulfonyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid-mjnohydratet med smp. 151 - 152°. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-benzen-sulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, 1) 36.65 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine are dissolved in 370 ml of 2-ni hydrochloric acid, and the solution is boiled for 6 hours under reflux. The solution is then evaporated in vacuo to dryness, and the resulting oil is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-benzenesulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride monohydrate is crystallized with m.p. 151 - 152°. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-benzenesulfonamide hydrochloride [lit.: E. Miller et al., J.am. chem. Soc. 62, 2101,

(1940)] og 20,5 g N-(2-brometyl)-N-isobutyl-cyanamid oppvarmes under rdring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk méd konsentrert natronlut, mettes.med hatriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid-monohydratet med smp. 151 - 152°. (1940)] and 20.5 g of N-(2-bromomethyl)-N-isobutyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The clear solution obtained is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and made acidic with saturated alcoholic hydrochloric acid. Upon cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride monohydrate is precipitated with m.p. 151 - 152°.

EKSEMPEL 21 EXAMPLE 21

39,7 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenklorid-opplosning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur opplosningen av 12,9 g valeriansyre-klorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenkloridfaser gir etter torking med natriumsulfat, filtrering og inndampning l-[p-(2-valeramido-etyl)-fenylsulfo-nyl]-2-imino-3-sek.butyl-imidazolidin-hemihydrat, som omkrystallisert fra eddikester smelter ved 111 - 113°. 39.7 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base is liberated with 300 ml of 2-n sodium hydroxide solution. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 12.9 g of valerian acid chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after drying with sodium sulfate, filtration and evaporation 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine hemihydrate, which is recrystallized from acetic ester melting at 111 - 113°.

På analog måte oppnår man fra 39,7 g l-[p-(2-aminoetyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidin-dihydroklorid og: 7,9 g acetylklorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 106 - 108°; 9,2 g propionylklorid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 11 g butyrylklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. In an analogous manner, one obtains from 39.7 g of l-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine dihydrochloride and: 7.9 g of acetyl chloride l-[p-( 2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine, m.p. 106 - 108°; 9.2 g of propionyl chloride 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine, m.p. 11 g of butyryl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine, m.p.

17,2 g cykloheksyl-acetylklorid l-[p-(2-cykloheksyl-acetamido- 17.2 g of cyclohexyl-acetyl chloride l-[p-(2-cyclohexyl-acetamido-

etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine,

smp. 111 - 113°; m.p. 111 - 113°;

18,5 g p-etoksybenzoylklorid l-[p-[2-(4-etoksybenzamido)-etyl]-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, 18.5 g of p-ethoxybenzoyl chloride l-[p-[2-(4-ethoxybenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine,

smp. 148 - 149,5°; m.p. 148 - 149.5°;

16,9 g 2 ,4-dime'tylbenzoylklorid l-[ p-[ 2-( 2,4-dimetyl-benzamido )-etyl]-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 120 - 122°; 16.9 g of 2,4-dimethylbenzoyl chloride 1-[p-[2-(2,4-dimethyl-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine, m.p. 120 - 122°;

22,8 g 3-metyl-O-acetyl-salicylsyreklorid l-[p-[2-(3-metyl-salicylamido)-etyl]-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 203,5 - 205; 22.8 g of 3-methyl-O-acetyl-salicylic acid chloride 1-[p-[2-(3-methyl-salicylamido)-ethyl]-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine, m.p. 203.5 - 205;

24,2 g 2-metoksy-5-tert.butyl-benzoylklorid l-[p-[2-(2-metoksy-5-tert.butyl-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-s ek. butyl-imidazolidinet, smp. 106 - 108°; 24.2 g 2-methoxy-5-tert.butyl-benzoyl chloride 1-[p-[2-(2-methoxy-5-tert.butyl-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-s ok. butyl-imidazolidine, m.p. 106 - 108°;

14,8 g benzoylklorid 1-[p-(2-benzamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 133 - 135°. 14.8 g of benzoyl chloride 1-[p-(2-benzamido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine, m.p. 133 - 135°.

b) Utgangsmaterialet 1-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidin-dihydrokloridet oppnås etter to b) The starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine dihydrochloride is obtained after two

fremgangsmåter: procedures:

1) 36,6 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inn-aampes så i vakuum til tbrrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-fenyl-sulfonyl] -2-imino-3-sek.butyl-imidazolidin-dihydrokloridet med smp. 250° (spaltning). 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert 1) 36.6 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine are dissolved in 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux . The solution is then evaporated in vacuo to dryness, and the resulting oil is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-phenyl-sulfonyl]-2-imino-3-sec.butyl-imidazolidine dihydrochloride is crystallized with m.p. 250° (cleavage). 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g powdered

kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-benzen-sulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, potassium hydroxide, 23.65 g p-(2-amino-ethyl)-benzenesulfonamide hydrochloride [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101,

(1940)] og 20,5 g N-(2-brom-etyl)-N-sek.butyl-cyanamid oppvarmes under roring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser tdrkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og aventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidin-dihydrokloridet med smp. 250° (spaltnin<g>). (1940)] and 20.5 g of N-(2-bromoethyl)-N-sec.butyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. On cooling and eventual dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine dihydrochloride is precipitated with m.p. 250° (splitnin<g>).

EKSEMPEL , 22 EXAMPLE , 22

41,5 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin-monohydrat opplbses i 200 ml vann, og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylen-klorid. Den med natriumsulfat torkede metylenklorid-opplbsning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur opplosningen av 7,9 g acetylklorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter tbrking med natriumsulfat, filtrering og inndampning l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin , som omkrystallisert fra eddikester smelter ved 127 - 129°.. 41.5 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine monohydrate is dissolved in 200 ml of water, and the base is released with 300 ml of 2-n sodium hydroxide solution. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 7.9 g of acetyl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after treatment with sodium sulfate, filtration and evaporation 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, which recrystallized from acetic ester melts at 127 - 129°..

EKSEMPEL 23 EXAMPLE 23

a) 41,5 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-tert. butyl-imidazolidin-dihydroklorid-monohydrat opplbses i 200 ml a) 41.5 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-tert. butyl imidazolidine dihydrochloride monohydrate is dissolved in 200 ml

vann, og basen frisettes, med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylen-klorid-opplbsning. tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur opplosningen av 13 g isoval-eriansyre-klorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n na-fronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man ,to ganger med metylen-klorid. De forente metylenklorid-faser gir etter tbrking med water, and the base is freed with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. The sodium sulfate-dried methylene chloride solution. 50.5 g of triethylamine are added. The solution of 13 g of isovaleric acid chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after treatment with

natriumsulfat, filtrering .og inndampning l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imida"olidin, som omkrystallisert fra eddikester smelter ved 152 - 154°. sodium sulfate, filtration .and evaporation 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imid"olidine, which recrystallized from acetic ester melts at 152 - 154°.

På analog måte oppnår man fra 41,5 g l-[p-(2-amino-etyl)-fenyl-sulf onyl.} -2- imino-3-tert.butyl-imidazolidin-dihydroklorid-monohydrat og: 13,0 g pivaloylklorid l-[p-(2-pivalamido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 140 - 142°; In an analogous manner, one obtains from 41.5 g of 1-[p-(2-amino-ethyl)-phenyl-sulfonyl.}-2-imino-3-tert-butyl-imidazolidine-dihydrochloride monohydrate and: 13.0 g pivaloyl chloride 1-[p-(2-pivalamido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 140 - 142°;

13.7 g 2-klorpropionylklorid l-[p-[2-(2-klorpropion-amido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, 13.7 g of 2-chloropropionyl chloride 1-[p-[2-(2-chloropropion-amido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine,

smp. 151 - 153°; m.p. 151 - 153°;

15,2 g 2-klorbutyrylklorid l-[ p-[ 2-(2-klorbutyramido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 142 - 144°; 15.2 g of 2-chlorobutyryl chloride 1-[p-[2-(2-chlorobutyramido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 142 - 144°;

15.8 g cykloheksan-karboksylsyreklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp^ 176.- 178°; 15.8 g of cyclohexane-carboxylic acid chloride 1-[p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, mp 176.-178°;

22.5 g a-,a ,a-trif luor-m-toluoylklorid l-[ p-( 2-a ,a ,a-trif luor-m-to lu amido-etyl)--f enylsulf onyl]-2-imino-3-tert. butyl-imidazolidinet, smp. 172 - 173°; 22.5 g a-,a,a-trifluoro-m-toluoyl chloride 1-[p-(2-a,a,a-trifluoro-m-toluamido-ethyl)--phenylsulfonyl]-2-imino -3-tert. butyl-imidazolidine, m.p. 172 - 173°;

16.6 g o-toluoylklorid l-[p-[2-(2-toluamido)-etyl]-fenylsulfo-nyl]-2-imino-3-te-rt.butyl-imidazolidinet,. smp. 1.60 - 161°; 16.6 g of o-toluoyl chloride 1-[p-[2-(2-toluamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert-butyl-imidazolidine,. m.p. 1.60 - 161°;

18.9 g o-klorbenzoylklorid l-[ p-[ 2-(.2-klorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp-. 152 - 154°; 18.9 g of o-chlorobenzoyl chloride 1-[p-[2-(.2-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 152 - 154°;

22>1 g 2-metoksy-5-klor-benz.oylklorid l-[p-[2-(2-metoksy-5-klorbenzamido)- etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 124 - 126°; 22>1 g 2-methoxy-5-chloro-benzoyl chloride 1-[p-[2-(2-methoxy-5-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine , m.p. 124 - 126°;

22,6 g 3,4-diklorbenzoylklorid l-[ p-[ 2- ( 3 ,4-diklorbenzarnido) - etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin et, smp. 168 - 170°; 22.6 g of 3,4-dichlorobenzoyl chloride 1-[p-[2-(3,4-dichlorobenzanido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine et, m.p. 168 - 170°;

24.5 g 3,4 ,5-trimetoksybenzoylklorid l-[ p-[ 2-( 3 ,4 ,5-trime'toksy-beozamido)- etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 130 - 132°; 24.5 g 3,4,5-trimethoxybenzoyl chloride 1-[p-[2-(3,4,5-trimethoxy-beozamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. . 130 - 132°;

18,2 g 2,5-dimetylbenzoylklorid l-[p-[2-(2,5-dimetylbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 152 - 154°; 18.2 g of 2,5-dimethylbenzoyl chloride 1-[p-[2-(2,5-dimethylbenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 152 - 154°;

11.6 g butyrylklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-amino-3-tert.butyl-imidazolidinet, smp. 148 - 149°; 11.6 g of butyryl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-amino-3-tert.butyl-imidazolidine, m.p. 148 - 149°;

18,0 g 2-metoksy-benzoylklorid l-[p-[2-(2-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 131 - 131,5°. 18.0 g of 2-methoxy-benzoyl chloride 1-[p-[2-(2-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 131 - 131.5°.

b) Utgangsmaterialet l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin-dihydroklorid-monohydrat oppnås b) The starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-tert-butyl imidazolidine dihydrochloride monohydrate is obtained

etter to fremgangsmåter: by two methods:

1) 36,65 g l-[p-(2 -acetamino-etyl)-f enylsulfonyl]-2-imino-3-tert.butyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres 1-[p-(2-amino-etyl)-benzensul fonyl]-2-imino-3-tert.butyl-imidazolidin-dihydroklorid-monohydratet med smp. 232 - 234°. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-fenylsulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, 1) 36.65 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine is dissolved in 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at backflow. The solution is then evaporated in vacuo to dryness, and the oil obtained is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-benzenesulfonyl]-2-imino-3-tert.butyl-imidazolidine dihydrochloride monohydrate with m.p. 232 - 234°. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-phenylsulfonamide hydrochloride [lit.: E. Miller et al., J.am.chem. Soc. 62, 2101,

(1940)] og 16 g N-(2-klor-etyl)-N-tert.butyl-cyanamid oppvarmes under roring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin-dihydroklorid-monohydratet med smp. (1940)] and 16 g of N-(2-chloro-ethyl)-N-tert.butyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. Upon cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine dihydrochloride monohydrate is precipitated with m.p.

232 - 234°. 232 - 234°.

EKSEMPEL 24 EXAMPLE 24

40,9 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylen-klorid. Den med" natriumsulfat torkede metylenklorid-opplosning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur opplosningen av 13,0 g n-valeryl-klorid i 100 ml metylenklorid i lopet. av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml. 2- n natronlut. og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenkloridfaser gir etter torking med natriumsulfat, filtrering og inndampning. l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3- cyklopentyl-imidazolidin,. som omkrystallisert fra aceton smelter ved 132; - 134°. 40.9 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base is liberated with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. Then, at room temperature, the solution of 13.0 g of n-valeryl chloride in 100 ml of methylene chloride is added dropwise in the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-N sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after drying with sodium sulphate, filtration and evaporation. l-[p -(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, as recrystallized from acetone melts at 132°-134°.

På analog, måte oppnår man fra 40,9 g l-[ p-( amino-etyl)-f enylsulf onyl]-2-imino-3-cyk lopen tyl-imida zol idin-dihydrok lorid og: 11 g butyrylklorid 1-fp-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cyklopen-tyI-imidazolidinet, smp. In an analogous manner, one obtains from 40.9 g of l-[p-(amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine-dihydrochloride and: 11 g of butyryl chloride 1- fp-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopen-thyI-imidazolidine, m.p.

14,5 g n-heksandyl-klorid l-[p-(2-heksanamido-etyl)-fenylsulfo-nyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 118 - 119°; 14.5 g of n-hexanedyl chloride 1-[p-(2-hexanamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 118 - 119°;

15,8 g cykloheksan-karboksylsyreklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-f enylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 178 - 179°; 15.8 g of cyclohexane-carboxylic acid chloride 1-[p-(2-cyclohexane-corboxamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 178 - 179°;

8,1 g acetylklorld I-[p-(2-acetamido-etyl).-fenylsulfonyl]-2- 8.1 g of acetyl chloride I-[p-(2-acetamido-ethyl).-phenylsulfonyl]-2-

imino-3-cyklopentyl-imidazolidinet, smp. 151 - 152°; the imino-3-cyclopentyl-imidazolidine, m.p. 151 - 152°;

18,5 g 2-klorbenzoylklorid l-[p-[2-(2-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 18.5 g of 2-chlorobenzoyl chloride 1-[p-[2-(2-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p.

187 - 190,5°; 187 - 190.5°;

22,5 g 2,4-diklorbenzoylklorid l-[p-[2-(2,4-diklor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 151,5 - 153°; 22.5 g of 2,4-dichlorobenzoyl chloride 1-[p-[2-(2,4-dichloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 151.5 - 153°;

16,5 g l-metyl-3-cykloheksen-karboksylsyre l-[p-[2-(l-metyl-3-cykloheksen-karboksamido)-etyl]-fenylsulfonyl]-2-imino-3-cyklo-pentyl-imidazolidinet, smp. 129 - 131°; 16.5 g of 1-methyl-3-cyclohexene-carboxylic acid l-[p-[2-(1-methyl-3-cyclohexene-carboxamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine , m.p. 129 - 131°;

16.7 g 1-metylcykloheksan-karboksylsyreklorid 16.7 g of 1-methylcyclohexane-carboxylic acid chloride

1"[ P"[2 - (1-met yl-cyk lohek sank årboks amido) - etyl]-f enylsulf onyl ].-2- imino-3-cyklopentyl-imidazolidinet, smp. 130 - 131°; 1"[ P"[2 - (1-Meth yl-Cyclohexan erbox amido)-ethyl]-phenylsulfonyl ].-2-imino-3-cyclopentyl-imidazolidine, m.p. 130 - 131°;

17.8 g 3-metoksybenzoylklorid l-[p-[2-(3-metoksy-benzamido)- etyl]-f enylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 146,5 - 148°; 17.8 g of 3-methoxybenzoyl chloride 1-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 146.5 - 148°;

21,0 g 3,4-dimetoksy-benzoylklorid l-[p-[2-(3,4-dimetoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3- cyklopentyl-imidazolidinet, smp. 180 - 182°. 21.0 g of 3,4-dimethoxy-benzoyl chloride 1-[p-[2-(3,4-dimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 180 - 182°.

b) Utgangsmaterialet l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin-dihydroklorid oppnås etter to b) The starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine dihydrochloride is obtained after two

f remgangsmå.ter: procedures:

1) 37,8 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-benzen-sulf on yl] -2-imino-3-cyklopentyl-imidazolidin-dihydrokloridet med smp. 270°. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-fenylsulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, 1) 37.8 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine are dissolved in 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux. The solution is then evaporated in vacuo to dryness, and the oil obtained is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-benzene-sulfonyl]-2-imino-3-cyclopentyl-imidazolidine dihydrochloride is crystallized with m.p. 270°. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-phenylsulfonamide hydrochloride [lit.: E. Miller et al., J.am.chem. Soc. 62, 2101,

(1940)] og 17,2 g N-(2-klor-etyl)-N-cyklopentyl-cyanamid'oppvarmes under roring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser tdrkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin-dihydrokloridet med smp. 270° (spaltning). (1940)] and 17.2 g of N-(2-chloro-ethyl)-N-cyclopentyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. On cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine dihydrochloride is precipitated with m.p. 270° (cleavage).

EKSEMPEL 25 EXAMPLE 25

a) 42,3 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og a) 42.3 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and

basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenklorid-opplbsning tilsettes 50,5 g trietylamin. Derpå tildrypper man ved værelsetemperatur opplosningen av 9,3 g propionsyreklorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenkloridfaser gir etter tbrking med natriumsulfat, filtrering og inndampning l-[p-(2-propionamido-etyl)-fenylsul-fonyl] -2-imino-3-cykloheksyl-imidazolidin-semihydrat , som omkrystallisert fra eddikester smelter ved 110 - 112°. the base is freed with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 9.3 g of propionic acid chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after treatment with sodium sulfate, filtration and evaporation 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine semihydrate, which recrystallized from acetic acid melts at 110 - 112°.

På analog måte oppnår man fra 42,3 g l-[p-(2-amino-etyl)-fenyl-sulf onyl] -2- iminp-3- cyk loheksyl -imida zol id in -dihydrok lo rid og: 8,0 g acetylklorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 181 - 183<0>; In an analogous manner, one obtains from 42.3 g of 1-[p-(2-amino-ethyl)-phenyl-sulfonyl]-2-imin p-3-cyclohexyl-imidazolidin-dihydrochloride and: 8, 0 g acetyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 181 - 183<0>;

10,7 g butyrylklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2- 10.7 g of butyryl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-

imino-3-cykloheksyl-imidazolidin-hemihydratet, smp. 143 - 144°; the imino-3-cyclohexyl-imidazolidine hemihydrate, m.p. 143 - 144°;

12,1 g valerylklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 154 - 155°; 12.1 g valeryl chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 154 - 155°;

12,1 g isovalerylklorid l-[p-(2-isovaleramido-etyl)-fenylsulfo-nyl]-2-imino-3-cykloheksyl-imidazolidinetsmp. 180 - 181°; 12.1 g of isovaleryl chloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine m.p. 180 - 181°;

10,5 g cyklopropan-karboksylsyreklorid l-[p-(2-cyklopropan-kårboksamidoetyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 172 - 173°; 10.5 g of cyclopropane carboxylic acid chloride 1-[p-(2-cyclopropane-boxamidoethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 172 - 173°;

18.4 g 3-cykloheksyl-propionylklorid l-[p-[2-(3-cykloheksyl-propionamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolldinet, smp. 168 - 169a; 18.4 g of 3-cyclohexyl-propionyl chloride 1-[p-[2-(3-cyclohexyl-propionamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazoldine, m.p. 168 - 169a;

17.5 g kanelsyreklorid 1-[p-(2-kanelsyre-amido-etyl)-fenylsulfo-nyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 182 - 183°; 17.5 g cinnamic acid chloride 1-[p-(2-cinnamic acid-amido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 182 - 183°;

15,0 g oc-klorbutyrylklorid l-[p-( 2-a-klorbutyramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 158 - 159°; 15.0 g o-chlorobutyryl chloride 1-[p-(2-a-chlorobutyramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 158 - 159°;

16,4 g p-toluylklorid 1 -[ p-[ 2-(2-toluamido)-etyl] - f enylsulf onyl] - 2-imino-3-cykloheksyl-imidazolidinet, smp. 198 - 199°; 16.4 g of p-toluyl chloride 1-[p-[2-(2-toluamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 198 - 199°;

18r5 g o-klorbenzoylklorid l-[p-[2-(2-klorbenzamido)-etyl]-fenylsulfonyl-2-imino-3-cykloheksyl-imidazolidinet, smp. 191 - 192°; 18r5 g o-chlorobenzoyl chloride 1-[p-[2-(2-chlorobenzamido)-ethyl]-phenylsulfonyl-2-imino-3-cyclohexyl-imidazolidine, m.p. 191 - 192°;

18,0 g o-metoRsybenzoylklorid l-[ p-[2-( 2-metoksybenzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 175 - 176°<;>18.0 g of o-methoRsybenzoyl chloride 1-[p-[2-(2-methoxybenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 175 - 176°<;>

18,0 g m-metoksybenzoylklorid l-[p-[2-(3-metoksybenzamido)-etyl]-fenylsulfonyl]-2-imino—3-cykloheksyl-imidazolidInet, smp. 167 - 168°; 18.0 g of m-methoxybenzoyl chloride 1-[p-[2-(3-methoxybenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolide, m.p. 167 - 168°;

17,8 g 2,5-dimetylbenzoylklorid l-[p-[2-(2,5-dimetyl-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 186 - 187°; 17.8 g of 2,5-dimethylbenzoyl chloride 1-[p-[2-(2,5-dimethyl-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 186 - 187°;

19.4 g p-etoksy-benzoylklorid l-[p-[2-(4-etoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 156 - 157,5°; 19.4 g of p-ethoxy-benzoyl chloride 1-[p-[2-(4-ethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 156 - 157.5°;

23,0 g o-brombenzoylklorid l-[p-[2-(2-brombenzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 179 - 181°; 23.0 g o-bromobenzoyl chloride 1-[p-[2-(2-bromobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 179 - 181°;

15.0 g 2-etyl-butyrylklorid l-[p-[2-(2-etyl-butyramido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 169 - 170°; 15.0 g of 2-ethyl-butyryl chloride 1-[p-[2-(2-ethyl-butyramido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 169 - 170°;

17.5 g 3-cykloheksyl-propionylklorid 1-[p-[2-(3-cykloheksyl-propionamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 168 - 169°; 17.5 g of 3-cyclohexyl-propionyl chloride 1-[p-[2-(3-cyclohexyl-propionamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 168 - 169°;

18,2 g p-metoksy-benzoylklorid l-[p-[2-(4-metoksy-benzamido)-etyl]-f enylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, 18.2 g p-methoxy-benzoyl chloride 1-[p-[2-(4-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine,

smp. 153 - 154°; m.p. 153 - 154°;

19.1 g 2-metyltio-benzoylklorid l-[p-[2-(2-metyltio-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 184 - 186°; 19.1 g of 2-methylthio-benzoyl chloride 1-[p-[2-(2-methylthio-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 184 - 186°;

21,5 g 3,4-diklor-benzoylklorid l-[p-[2-(3,4-diklor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 227 - 228°; 21.5 g of 3,4-dichloro-benzoyl chloride 1-[p-[2-(3,4-dichloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 227 - 228°;

21,0 g 2-metoksy-5-klor-benzoylklorid l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 167 - 170°; 21.0 g of 2-methoxy-5-chloro-benzoyl chloride 1-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. . 167 - 170°;

16,5 g l-metyl-3-cykloheksen-karboksylsyreklorid l-[p-[2-(l-metyl-3-cykloheksen-kårboksamido)-etyl]-fenylsulfonyl]-2-imino- 16.5 g of 1-methyl-3-cyclohexene-carboxylic acid chloride 1-[p-[2-(1-methyl-3-cyclohexene-carboxamido)-ethyl]-phenylsulfonyl]-2-imino-

3-cykloheksyl-imidazolidinet, smp. 158 - 160°; 3-Cyclohexyl-imidazolidine, m.p. 158 - 160°;

16,5 g 4-metyl-3-cykloheksen-karboksylsyreklorid l-[p-[2-(4-metyl-3-cykloheksen-karboksamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 200 - 201°; 16.5 g of 4-methyl-3-cyclohexene-carboxylic acid chloride 1-[p-[2-(4-methyl-3-cyclohexene-carboxamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. . 200 - 201°;

15,0 g cykloheksankarboksylsyreklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-fenylsulfonyl]-2-im.ino-3-cykloheksyl-imidazolidinet, smp. 208 - 209°; 15.0 g of cyclohexanecarboxylic acid chloride 1-[p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 208 - 209°;

16,3 g 1-metyl-cykloheksan-karboksylsyreklorid l-[p-[2-(l-metyl-cykloheksan-kårboksamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 162 - 163°; l-[p-[2-(3,4-dimetoksy-benzamido)-etyl]- fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 203 - 205°. 16.3 g of 1-methyl-cyclohexane-carboxylic acid chloride 1-[p-[2-(1-methyl-cyclohexane-carboxamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 162 - 163°; 1-[p-[2-(3,4-dimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 203 - 205°.

b) Utgangsmaterialet l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid oppnås etter to b) The starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine dihydrochloride is obtained after two

fremgangsmåter: procedures:

1) 39,2 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin opplbses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelbp. Opplosningen inndampes så i vakuum til tbrrhet, og den erholdte olje opplbses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)- - fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydrokloridet, smp. 247 - 250°. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 23,65 g p-(2-amino-etyl)-benzensulfonamid-hydroklorid [lit.: E. Miller et al., J.am.chem.Soc. 62, 2101, 1) 39.2 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine are dissolved in 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux. The solution is then evaporated in a vacuum to dryness, and the resulting oil is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)--phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine dihydrochloride crystallizes out, m.p. 247 - 250°. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 23.65 g of p-(2-amino-ethyl)-benzenesulfonamide hydrochloride [lit.: E. Miller et al., J.am.chem. Soc. 62, 2101,

(1940)] og 23,1 g N-(2-brom-etyl)-N-cykloheksyl-cyanamid oppvarmes under rbring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydrokloridet med smp. 247 - 250°. (1940)] and 23.1 g of N-(2-bromoethyl)-N-cyclohexylcyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. On cooling and possible dilution with ether, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine dihydrochloride is precipitated with m.p. 247 - 250°.

EKSEMPEL 26 EXAMPLE 26

a) Analogt eksempel 25a) oppnår man fra 43,7 g l-[p-(amino-etyl)-f enylsulfonyl]-2-imino-3-cykloheptyl-imidazolidin-dihydroklorid og 7,9 g acetylklorid l-[p-(2-acetamido-etyl)-fenylsulfo-nyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 166 - 167°. a) Analogous to example 25a) one obtains from 43.7 g of l-[p-(amino-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine dihydrochloride and 7.9 g of acetyl chloride l-[p- (2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 166 - 167°.

Fra den samme aminoforbindelse oppnår man fra: From the same amino compound one obtains from:

11,0 g butyrylklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 12,3 g valerylklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 145 - 147°; 18,2 g 3-metoksybenzoylklorid l-[p-[2-(3-metoksybenzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 164,5°; 17,8 g 2,4-dimetylbenzoylklorid l-[p-[2-(2,4-dimetylbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 187 - 189°; l-[p-[2-(3,4-dimetoksy-benzamido)-etyl]-f enylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 208 - 210°. 11.0 g of butyryl chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 12.3 g valeryl chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 145 - 147°; 18.2 g of 3-methoxybenzoyl chloride 1-[p-[2-(3-methoxybenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 164.5°; 17.8 g of 2,4-dimethylbenzoyl chloride 1-[p-[2-(2,4-dimethylbenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 187 - 189°; 1-[p-[2-(3,4-dimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 208 - 210°.

b) Utgangsmaterialet l-[p-(amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidin-dihydroklorid fremstilles analogt b) The starting material 1-[p-(amino-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine dihydrochloride is prepared analogously

25b) fra 40,6 g 1-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidin-dihydroklorid; smp. 280° (spaltning). 25b) from 40.6 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine dihydrochloride; m.p. 280° (cleavage).

EKSEMPEL 27 EXAMPLE 27

a) 41,1 g l-[p-(3-amino-propyl)-fenylsulfonyl]- 2-imino-3-butyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen a) 41.1 g of 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base

frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenklorid-oppldsning tilsettes 50,5 g trietylamin. Deretter tildrypper man ved værelsetemperatur opplosningen av 13 g isovalerylklorid i 100 ml metylenklorid i lopet av 20- minutter. Etter at opplosningen er rort i 1. time ved værelsetemperatur, vasker man den med 100 ml free with 300 ml 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 13 g of isovaleryl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml

2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter tdrking med natriumsulfat, filtrering og inndampning l-[p-(3-isovaleramido-propyl)-fenyl-sulfonyl]-2 -imino-3-butyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 101 - 103°. 2-n caustic soda and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after drying with sodium sulfate, filtration and evaporation 1-[p-(3-isovaleramido-propyl)-phenyl-sulfonyl]-2-imino-3-butyl-imidazolidine, which recrystallized from acetic ester melts at 101 - 103°.

På analog måte oppnår man fra 41,1 g l-[ p- (.3-amino-propyl) - f enylsulfonyl]-2-imino-3-butyl-imidazolidin og: 22,0 g 2-metoksy-5-klor-benzoylklorid l-[ p-[3-(2-meto.ksy-5-klorbenzamido)-propyl]-f enylsulfonyl]-2-imino-3-butyl-imidazolidinet, som olje; 18,2 g 3,5-dimetyl-benzoylklorid l-[p-[3-(3,5-dimetyl-benzamido)-propyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 96 - 100°. b) Utgangsmaterialet l-[p-(3-amino-propyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin-dihydroklorid oppnås etter to fremgangsmåter: 1) 38,0 g l-[p-(3-acetamino-propyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(3-amino-propyl)-fenylsulfonyl]- 2-imino-3-butyl-imidazoiidin-dihydrokloridet som meget hygroskopiske krystaller. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 250 g p-(3-amino-propyl)-benzensulfonamid-hydroklorid [lit.: E. Muller, Angew.Chemie, 61, 179, (1949)] og 16 g N-(2-klor-etyl)-N-butyl-cyanamid oppvarmes under roring i 1. time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Ved avkjoling og eventuell fortynning med eter utfelles l-[p-(3-amino-propyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidin-dihydrokloridet som meget hygroskopiske krystaller. In an analogous manner, one obtains from 41.1 g of 1-[p-(.3-amino-propyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine and: 22.0 g of 2-methoxy-5-chloro -benzoyl chloride 1-[p-[3-(2-methoxy-5-chlorobenzamido)-propyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, as oil; 18.2 g of 3,5-dimethyl-benzoyl chloride 1-[p-[3-(3,5-dimethyl-benzamido)-propyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 96 - 100°. b) The starting material l-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride is obtained by two methods: 1) 38.0 g of l-[p-(3-acetamino -propyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine is dissolved in 370 ml of 2-n hydrochloric acid, and the solution is refluxed for 6 hours. The solution is then evaporated in vacuo to dryness, and the oil obtained is dissolved in alcohol. In the cold, l-[p-(3-amino-propyl)-phenylsulfonyl]- The 2-imino-3-butyl-imidazoiidine dihydrochloride as highly hygroscopic crystals. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 250 g of p-(3-amino-propyl)-benzenesulfonamide hydrochloride [lit.: E. Muller, Angew.Chemie, 61, 179, (1949) ] and 16 g of N-(2-chloro-ethyl)-N-butyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. On cooling and possible dilution with ether, the 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine dihydrochloride precipitates as very hygroscopic crystals.

EKSEMPEL 28 EXAMPLE 28

a) 41,1 g l-[ p-(3-amino-propyl)-f enylsulf onyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og a) Dissolve 41.1 g of 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride in 200 ml of water, and

basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenklorid-opplosning tilsettes 50,5 g trietylamin. Derpå tildrypper man ved værelsetemperatur opplosningen av 13 g pivaloyl-klorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metyl enkloridfas er gir etter torking med natriumsulfat, filtrering og inndampning l-[p-(3-pivalamido-propyl)-fenylsulfo-nyl]-2-imino-3-isobutyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 112 - 113°. the base is freed with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 13 g of pivaloyl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methyl chloride phase gives, after drying with sodium sulfate, filtration and evaporation, 1-[p-(3-pivalamido-propyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, which recrystallized from ethyl acetate melts at 112 - 113°.

b) Utgangsmaterialet l-[p-(3-amino-propyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin-dihydroklorid oppnås etter to b) The starting material 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride is obtained after two

fremgangsmåter: procedures:

1) 38,0 g l-[p-(3-acetamino-propyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje l-[p-(3-amino-propyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidin-dihydrokloridet anvendes rått. 2) En blanding av 100 ml dimetylsulfoksyd, 11,2 g pulverisert kaliumhydroksyd, 25,0 g p-(3-amino-propyl)-benzensulfonamid-hydroklorid [lit.: E. Muller Angew.Chem. 61, 179 (1949)] og 20,5 g N-(2-brom-etyl)-N-isobutyl-cyanamid oppvarmes under roring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning ekstraheres med konsentrert natronlut; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Etter inndampning oppnår man 1-[p-(3-amino-propyl)-fenylsulfo-nyl]-2-imino-3-isobutyl-imidazolidin-dihydrokloridet som olje. 1) 38.0 g of 1-[p-(3-acetamino-propyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine are dissolved in 370 ml of 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux. The solution is then evaporated in vacuo to dryness, and the obtained oil 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride is used crudely. 2) A mixture of 100 ml of dimethyl sulfoxide, 11.2 g of powdered potassium hydroxide, 25.0 g of p-(3-amino-propyl)-benzenesulfonamide hydrochloride [lit.: E. Muller Angew.Chem. 61, 179 (1949)] and 20.5 g of N-(2-bromoethyl)-N-isobutylcyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The clear solution obtained is extracted with concentrated caustic soda; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. After evaporation, the 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine dihydrochloride is obtained as an oil.

EKSEMPEL 29 EXAMPLE 29

41,1 g l-[ p-(3-amino-propyl)-fenylsulfonyl]-2-imino-3-tert. butyl-imidazolidin-dihydroklorid opplbses 1 20O ml vann, og. basen frisettes med 300 ml 2-n natronlut.. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metylenklorid-opplbsning. tilsettes 50,5 g trietylamin. Derpå tildrypper man ved værelsetemperatur opplosningen av 18,2 g 3,4-dimetyl-benzoylklorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter tbrking med natriumsulfat, filtrering og inndampning l-[p-[3-(3,4-dimetyl-benzamido)-propyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 144 - 146°. 41.1 g of 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-tert. butyl imidazolidine dihydrochloride is dissolved in 1 200 ml of water, and. the base is freed with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. The sodium sulfate-dried methylene chloride solution. 50.5 g of triethylamine are added. The solution of 18.2 g of 3,4-dimethylbenzoyl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2N caustic soda and twice with water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give after treatment with sodium sulfate, filtration and evaporation 1-[p-[3-(3,4-dimethyl-benzamido)-propyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, as recrystallized from acetic ester melts at 144 - 146°.

b) Utgangsmaterialet l-[p-(3-amino-propyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidin-dihydroklorid oppnås etter to b) The starting material 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine dihydrochloride is obtained after two

fremgangsmåter: procedures:

1) 38,0 g l-[p-(3-acetamino-propyl)-fenylsulfonyl]-2-imino-3-. tert.butyl-imidazolidin opplbses i 370 ml. 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelbp. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje l-[p-(3-amino-propyl)-benzensulfonyl]-2-imino-3-tert.butyl-imidazolidin-dihydrok lorid anvendes rå. 1) 38.0 g of 1-[p-(3-acetamino-propyl)-phenylsulfonyl]-2-imino-3-. tert-butyl-imidazolidine is dissolved in 370 ml. 2-n hydrochloric acid, and the solution is boiled for 6 hours at reflux. The solution is then evaporated in vacuo to dryness, and the oil obtained 1-[p-(3-amino-propyl)-benzenesulfonyl]-2-imino-3-tert.butyl-imidazolidine dihydrochloride is used crude.

2.) En blanding av 100 ml dimetylsulf oksyd, 11,2 g pulverisert 2.) A mixture of 100 ml dimethylsulfoxide, 11.2 g powdered

kaliumhydroksyd, 25,0 g p-(3-amino-propyl)-benzen-sulfonamid-hydroklorid [lit.: E. Muller, Angew.Chem. 61, 179 (1949)] og 16 g N-(2-klor-etyl)-N-tert.butyl-cyanamid oppvarmes under roring i 1 time i oljebad til 110°. Etter avkjoling heller man på vann. Den erholdte blakke opplosning innstilles alkalisk med konsentrert natronlut, mettes med natriumklorid og ekstraheres tre ganger med metylenklorid; de organiske faser torkes over natriumsulfat, filtreres og inndampes. Den erholdte olje (fri base) opploses i alkohol og innstilles sur med mettet alkoholisk saltsyre. Etter inndampning oppnår man l-[p-(3-amino-propyl) -f enylsulfonyl] - 2- imino-3-tert. bu tyl-imida zol idin-dihydrokloridet som olje. potassium hydroxide, 25.0 g p-(3-amino-propyl)-benzenesulfonamide hydrochloride [lit.: E. Muller, Angew.Chem. 61, 179 (1949)] and 16 g of N-(2-chloro-ethyl)-N-tert-butyl-cyanamide are heated with stirring for 1 hour in an oil bath to 110°. After cooling, pour on water. The resulting clear solution is made alkaline with concentrated caustic soda, saturated with sodium chloride and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and evaporated. The obtained oil (free base) is dissolved in alcohol and acidified with saturated alcoholic hydrochloric acid. After evaporation, 1-[p-(3-amino-propyl)-phenylsulfonyl]-2-imino-3-tert is obtained. the butyl imidazolidine dihydrochloride as an oil.

EKSEMPEL 30 EXAMPLE 30

a) 41,1 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og a) 41.1 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and

basen frisettes med 300 ml 2-n natronlut. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metyl enklorid-opplosning tilsettes 50,5 g trietylamin. Derpå tildrypper man ved værelsetemperatur opplosningen av 12,7 g valeryl-klorid i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter tbrking med natriumsulfat, filtrering og inndampning l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidin, som omkrystallisert fra eddikester smelter ved 108 - 110°. the base is freed with 300 ml of 2-n caustic soda. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 12.7 g of valeryl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give, after treatment with sodium sulfate, filtration and evaporation, 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine, which recrystallized from acetic ester melts at 108 - 110°.

På analog måte oppnår man fra 41,1 g l-[p-(2-amino-etyl)-fenyl-sul fonyl]-2-imino-3-buty1-4-metyl-imidazolidin-dihydroklorid og: 12,7 g isovalerylklorid l-[p-(2-isovaleramido-etyl)-fenylsulfo-nyl]-2-imino-3-butyl-4-metyl-imidazolidinet, smp. 102 - 103°; In an analogous manner, one obtains from 41.1 g of 1-[p-(2-amino-ethyl)-phenyl-sulfonyl]-2-imino-3-butyl1-4-methyl-imidazolidine dihydrochloride and: 12.7 g isovaleryl chloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine, m.p. 102 - 103°;

15,4 g cykloheksan-karboksylsyreklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidinet, smp. 137 - 139°; 15.4 g of cyclohexane-carboxylic acid chloride 1-[p-(2-cyclohexane-corboxamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine, m.p. 137 - 139°;

16,3 g o-toluoylklorid l-[p-[2-(2-toluamido)-etyl]-fenylsulfo-nyl]-2-imino-3-butyl-4-metyl-imidazolidin-hemihydratet, smp. 16.3 g o-toluoyl chloride 1-[p-[2-(2-toluamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine hemihydrate, m.p.

103 - 105°; 103 - 105°;

23,7 g o-brom-benzoylklorid l-[ p-[ 2-( 2-brombenzarnido) - etyl]-fenylsulfonyl]-2-imino-3-buty1-4-metyl-imidazolidinet, smp. 23.7 g o-bromo-benzoyl chloride 1-[ p-[ 2-( 2-bromobenzarnido)-ethyl]-phenylsulfonyl]-2-imino-3-buty1-4-methyl-imidazolidine, m.p.

100 - 102°v 100 - 102°w

18r0 g 3,5-dimetyl-benzoylkbrid l-[p-[2-(3,5-dlmetyl-benzamido)-etyl]-f enylsulfonyl}-2-imino-3-butyl-4-metyl-imidazo1idin, 18r0 g 3,5-dimethyl-benzoyl chloride 1-[p-[2-(3,5-dlmethyl-benzamido)-ethyl]-phenylsulfonyl}-2-imino-3-butyl-4-methyl-imidazo1idine,

smp. "138 - -140°v m.p. "138 - -140°w

7,9 g acetylklorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyI-imidazolidinet, smp. 132 - 133°; 7.9 g of acetyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine, m.p. 132 - 133°;

18,2 g 2,4-dimetyl-benzoylklorid l-[ p-[ 2-( 2 ,4-dimetyl-benzamido)-.etyl]-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidinet 1/4 H20, smp. 108 - 110°". 18.2 g of 2,4-dimethyl-benzoyl chloride 1-[p-[2-(2,4-dimethyl-benzamido)-.ethyl]-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine 1 /4 H 2 O, m.p. 108 - 110°".

b) Utgangsmaterial et l-[p-(2-amino-etyl)-f enylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidin-dihydroklorid oppnås etter b) Starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine dihydrochloride is obtained after

folgende fremgangsmåte: following procedure:

38,0 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolldin opploses i 370 ml 2-n saltsyre, og. opplosningen kokes i 6 timer ved tilbakeldp. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-metyl-imidazolidin-dihydrokiorIdet med smp. 240° 38.0 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine is dissolved in 370 ml of 2-n hydrochloric acid, and. the solution is boiled for 6 hours at reflux. The solution is then evaporated in vacuo to dryness, and the oil obtained is dissolved in alcohol. In the cold, 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-methyl-imidazolidine dihydrochloride is crystallized with m.p. 240°

(spaltning);. (cleavage);.

EKSEMPEL 31 EXAMPLE 31

a) På analog måte til eksempel 30a) oppnår man fra 41,1 g l-[p-(2- amino - et yl) - f enylsulfonyl] -2-imino-3- bu tyl-5-metyl- im idazoli--din og: 7,9 g acetylklorid 1-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-5-metyl-imidazolidinet, smp. 98 - 99°; 12,5 g valerylklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-5-metyl-imidazolidinet, smp. 95 - 97°; 12,5 g isovalerylklorid 1-[p-(2-isovaleramido-etyl)-fenylsulfo-nyl]-2-imino-3-butyl-5-metyl-imidazolidinet, smp. 131 - 133°; 14,1 g 2-etyl-butyrylklorid l-[p-[2-(2-etylbutyramido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-5-metyl-imidazolidinet, smp. 89 - 90°; a) In an analogous manner to example 30a), one obtains from 41.1 g 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazol- -dine and: 7.9 g of acetyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 98 - 99°; 12.5 g of valeryl chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 95 - 97°; 12.5 g isovaleryl chloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 131 - 133°; 14.1 g of 2-ethyl-butyryl chloride 1-[p-[2-(2-ethylbutyramido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 89 - 90°;

16,5 g 2-toluoylklorid 1-[p-[2-(2-toluamino)-etyl]-fenylsulfo-nyl]-2-imino-3-butyl-5-metyl-imidazolidinet, smp. 122 - 124°; 16.5 g of 2-toluoyl chloride 1-[p-[2-(2-toluamino)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 122 - 124°;

22,0 g 2-brombenzoylklorid l-[p-(2-brombenzamido-etyl)-fenyl-su lfonyl]-2 -imino-3-butyl-5-metyl-imidazolidinet, smp. 105 - 107°; 22.0 g of 2-bromobenzoyl chloride 1-[p-(2-bromobenzamido-ethyl)-phenyl-sulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 105 - 107°;

15,5 g cykloheksan-karboksylsyreklorid l-[ p-[2-(2-cyk lohek s an-ka rboks amido )-etyl]-fenylsulfonyl]-2-imino-3-butyl-5-metyl-imidazolidinet, smp. 127 - 129°. 15.5 g of cyclohexane-carboxylic acid chloride 1-[p-[2-(2-cyclohexan-carboxamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine, m.p. 127 - 129°.

b) U.tgangsmaterialet l-[ p- ( 2-amino-etyl )-f enylsulf onyl]-2-imino-3-buty1-5-metyl-imidazolidin-dihydroklorid fremstilles b) The starting material 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl 1-5-methyl-imidazolidine dihydrochloride is prepared

analogt 29b) fra 38,0 g l-[ p-( 2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-butyl-5-metyl-imidazolidin-dihydroklorid, smp. 255 - 257°. analogous to 29b) from 38.0 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-5-methyl-imidazolidine dihydrochloride, m.p. 255 - 257°.

EKSEMPEL 32 EXAMPLE 32

a) På analog måte til eksempel 30a) oppnår man fra 43,7 g 1-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-5-metyl-imidazolidin-dihydroklorid og 10,7 g butyrylklorid l-[p-(2-butyramido-etyl}-fenylsulfonyl]-2-imino-3-cykloheksyl-5-metyl-imidazolidinet, smp. 109 - 111°. b) Utgangsmaterialet l-[ p-( 2-amino-etyl )•-f enylsulf onyl]-2-imino-3-cykloheksyl-D-metyl-imidazolidin-dihydroklorid fremstilles analogt 29b) fra 40,6 g l-[p-(2-acetamino-etyl)-fenyl-sulf onyl]-2-imino-3-cykloheksyl-5-metyl-imidazolidin-dihydroklorid, olje. a) In an analogous manner to example 30a), one obtains from 43.7 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-5-methyl-imidazolidine dihydrochloride and 10, 7 g of butyryl chloride l-[p-(2-butyramido-ethyl}-phenylsulfonyl]-2-imino-3-cyclohexyl-5-methyl-imidazolidine, m.p. 109 - 111°. b) The starting material l-[ p-( 2 -amino-ethyl )•-phenylsulfonyl]-2-imino-3-cyclohexyl-D-methyl-imidazolidine dihydrochloride is prepared analogously to 29b) from 40.6 g of 1-[p-(2-acetamino-ethyl)-phenyl -sulfonyl]-2-imino-3-cyclohexyl-5-methyl-imidazolidine dihydrochloride, oil.

EKSEMPEL 33 EXAMPLE 33

42,5 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-etyl-imidazolidin-dihydroklorid opploses i 200 ml vann, og basen frisettes- med 300 ml 2-n natronlut.. Den ekstraheres med metylenklorid. Den med natriumsulfat torkede metyl enklorid-opplosning tilsettes .50,5 g trietylamin. Derpå- tildrypper man ved værelsetemperatur opplosningen .av 13 g valeryl-klorld i 100 ml metylenklorid i lopet av 20 minutter. Etter at opplosningen er rort i 1 time ved værelsetemperatur, vasker man den med 100 ml 2-n natronlut og to ganger med 100 ml vann. De vandige faser ekstraherer man to ganger med metylenklorid. De forente metylenklorid-faser gir etter tdrking-med natriumsulfat, filtrering og inndampning l-[ p-( 2-val eramido-etyl)-f enylsulf onyl}-2-imino-3-butyl-4-etyl-imidazolidin, som omkrystallisert fra eter/eddikester smelter ved' 92 - 94°. 42.5 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine dihydrochloride are dissolved in 200 ml of water, and the base is liberated with 300 ml of 2- n caustic soda.. It is extracted with methylene chloride. 50.5 g of triethylamine is added to the sodium sulfate-dried methylene chloride solution. The solution of 13 g of valeryl chloride in 100 ml of methylene chloride is then added dropwise at room temperature over the course of 20 minutes. After the solution has been stirred for 1 hour at room temperature, it is washed with 100 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. The aqueous phases are extracted twice with methylene chloride. The combined methylene chloride phases give, after drying with sodium sulfate, filtration and evaporation, 1-[p-(2-valeramido-ethyl)-phenylsulfonyl}-2-imino-3-butyl-4-ethyl-imidazolidine, which is recrystallized from ether/acetic acid melts at' 92 - 94°.

På analog måte oppnår man. fra 42,5 g 1-[p-(2-amino-etyl)-f enylsulfonyl]-2-imino-3-butyl-4-etyl-imidazolidin-dihydroklorid og: 11,5 g isobutyrylklorid l-[p-(2-isobutyramido-etyl)-fenylsulfo-nyl]-2-imino-3-butyl-4-etyl-imidazolidinet som olje; In an analogous way, one obtains from 42.5 g of 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine dihydrochloride and: 11.5 g of isobutyryl chloride 1-[p-( 2-isobutyramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine as an oil;

13,0 g piva-loylklorid l-[ p-( 2-pivalamido-etyl)-f enylsulf onyl]-2-imino-3-butyl-4-etyl-imidazolidinet, smp. 140 - 142°; 13.0 g of pivaloyl chloride 1-[p-(2-pivalamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine, m.p. 140 - 142°;

15,2 g 2-klor-Dutyrylklorid. l-[ p-[ 2-( 2-klor-butyramido )> etyl] - ' 15.2 g of 2-chloro-Dutyryl chloride. l-[p-[2-(2-chloro-butyramido)>ethyl]-'

fenylsulfonyl]-2-imino-3-butyl-4-etyl-imidazolidinet som olje; phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine as an oil;

22,6 g 2,5-diklor-benzoylklorid l-[p-[2-(2,5-diklor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-4-etyl-imidazolidinet som olje. 22.6 g of 2,5-dichloro-benzoyl chloride 1-[p-[2-(2,5-dichloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine as oil .

b) Utgangsmaterialet l-[ p-(-2-amino-etyl)-f enylsulf onyl]-2-imino-3-butyl-4-etyl-imidazolidin-dihydroklorid oppnås etter b) The starting material 1-[p-(-2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine dihydrochloride is obtained after

folgende fremgangsmåte: following procedure:

39,4 g l-[p-(2-acetamino-etyl)-fenylsulfonyl]-2-imino-3-butyl-4-etyl-imidazolidin opploses i 370 ml 2-n saltsyre, og opplosningen kokes i 6 timer ved tilbakelop. Opplosningen inndampes så i vakuum til torrhet, og den erholdte olje opploses i alkohol. I kulden utkrystalliseres l-[p-(2-amino-etyl)-fenylsul-fonyl] -2- imino-3- bu tyl -4 -etyl- im id azolidin-dihydro kloridet med smp. 222 - 224°. 39.4 g of 1-[p-(2-acetamino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine are dissolved in 370 ml of 2-n hydrochloric acid, and the solution is refluxed for 6 hours . The solution is then evaporated in vacuo to dryness, and the oil obtained is dissolved in alcohol. In the cold, the 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-butyl-4-ethyl-imidazolidine-dihydro chloride is crystallized with m.p. 222 - 224°.

EKSEMPEL 34 EXAMPLE 34

28 ml 4-n natronlut og 4,3 g etylenimin avkjoles til -10°. Deretter tilsettes en suspensjon av 26,2 g p-(2-acetamidoetyl)-fenylsulfoklorid i 100 ml aceton under roring og avkjoling, slik at temperaturen ikke stiger over 0°. Etter avsluttet tildrypning vidererbres i 30 minutter ved 0°. Deretter fjernes kjolebadet, og opplosningen av det erholdte l-[p-(2-acetamido-etyl)-fenylsulfonyl]-aziridin tilsettes 100 ml n-propylamin. Temperaturen stiger til 40 - 50°. Reaksjonsblandingen rbres videre i 1 time og deretter avdestilleres det overskytende amin i rotasjonsfordamper. Krys tallgroten, som ved siden av koksalt inneholder det onskede N-^-[ p-( 2-acetamido-etyl)-f enylsulf onyl] - N2-n-propyl-etylendiamin, opploses i 56 ml 2-n natronlut og tilsettes under roring porsjonsvis 10,6 g bromcyan, idet man ikke lar temperaturen stige over 40°. Etter 1 time ekstraheres den erholdte substans med metylenklorid, vaskes med 20 ml 2-n natronlut og to ganger med 100 ml vann. Etter torking og inndampning av metylenkloridopplosningen omkrystalliseres resten fra eddikester og gir l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet med smp. 138 - 140°. 28 ml of 4-n caustic soda and 4.3 g of ethyleneimine are cooled to -10°. A suspension of 26.2 g of p-(2-acetamidoethyl)-phenylsulfochloride in 100 ml of acetone is then added while stirring and cooling, so that the temperature does not rise above 0°. After completion of instillation, stirring continues for 30 minutes at 0°. The dressing bath is then removed, and the solution of the obtained 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-aziridine is added to 100 ml of n-propylamine. The temperature rises to 40 - 50°. The reaction mixture is further stirred for 1 hour and then the excess amine is distilled off in a rotary evaporator. The tallow root, which contains the desired N-^-[p-(2-acetamido-ethyl)-phenylsulfonyl]-N2-n-propyl-ethylenediamine in addition to common salt, is dissolved in 56 ml of 2-n caustic soda and added under stirring in portions 10.6 g of cyanogen bromide, not allowing the temperature to rise above 40°. After 1 hour, the substance obtained is extracted with methylene chloride, washed with 20 ml of 2-N caustic soda and twice with 100 ml of water. After drying and evaporating the methylene chloride solution, the residue is recrystallized from ethyl acetate to give 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine with m.p. 138 - 140°.

EKSEMPEL 35 EXAMPLE 35

28 ml 4-n natronlut og 4,3 g etylenimin avkjoles til -10 . Derpå tilsettes en suspensjon av 27,6 g p-(2-propionamidoetyl)-fenylsulfoklorid' i 100 ml aceton under roring og a-vkjoling, slik at temperaturen ikke stiger over 0°. Etter avsluttet tildrypning vidererdres i 30 minutter ved 0°. Deretter fjernes kjolebadet, og opplosningen av det erholdte l-[p-(2-propionamido-etyl)-fenylsulfonyl]-aziridin tilsettes 100 ml n-propylamin. Temperaturen stiger til 40 - 50°. Reaks.jonsblandingen rores videre i 1 time og deretter avdestilleres'det overskytende amin i. rotasjonsfordamper. Krystallgroten, som ved siden av koksalt inneholder det onskede N^-[p-(2-propionamido-etyl)-f enylsulfonyl]-^-n-propyl-etylendiamin, opploses i 56 ml 2-n natronlut og under roring tilsettes' porsjonsvis 10,6 g brom-, cyan, idet man ikke lar temperaturen stige over' 40°. Etter. 1 time ekstraheres den erholdte substans med metylenklorid, vaskés med 20 ml 2-n natronlut og to ganger med 100 ml vann. Etter tdrking og inndampning av metylenkloridopplosningen om-krystal1 iseres resten fra eddikester og gir 1-[p-(2-propion-am i do-etyl).-f enylsulf onyl]-2-imino-3-n-propyl-imida zol idinet med smp. 127 - 128p. 28 ml of 4-n caustic soda and 4.3 g of ethyleneimine are cooled to -10 . A suspension of 27.6 g of p-(2-propionamidoethyl)-phenylsulfochloride' in 100 ml of acetone is then added with stirring and cooling, so that the temperature does not rise above 0°. After completion of the instillation, stir for 30 minutes at 0°. The dressing bath is then removed, and the solution of the obtained 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-aziridine is added to 100 ml of n-propylamine. The temperature rises to 40 - 50°. The reaction mixture is further stirred for 1 hour and then the excess amine is distilled off in a rotary evaporator. The crystal grain, which contains the desired N^-[p-(2-propionamido-ethyl)-phenylsulfonyl]-^-n-propyl-ethylenediamine in addition to sodium chloride, is dissolved in 56 ml of 2-n caustic soda and, while stirring, is added portionwise 10.6 g of bromine, cyan, not allowing the temperature to rise above 40°. After. The substance obtained is extracted for 1 hour with methylene chloride, washed with 20 ml of 2-n sodium hydroxide solution and twice with 100 ml of water. After drying and evaporating the methylene chloride solution, the residue is recrystallized from acetic ester and gives 1-[p-(2-propion-amido-ethyl).-phenylsulfonyl]-2-imino-3-n-propyl-imidazole idine with m.p. 127 - 128p.

På analog måte oppnår man fra 100 ml propylamin og 29 g p-(2-butyramido-etyl)-fenylsulfoklorid l-[p-(2-butyramido-etyl)-f enylsulf onyl]-2-imino-3-pr'opyl-imidazolidinet, smp. 114 - 116°. In an analogous manner, one obtains from 100 ml of propylamine and 29 g of p-(2-butyramido-ethyl)-phenylsulfochloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-propyl -imidazolidine, m.p. 114 - 116°.

EKSEMPEL. 36 EXAMPLE. 36

28 ml 4-n natronlut og 4,3 g etylenimin avkjoles til -10 . Derpå tilsettes en suspensjon av 35,5 g p-[2-(2-métoksy-benzamido)-etyl]-fenylsulfoklorid i 100 ml'aceton under roring og avkjoling, slik at temperaturen ikke stiger over 0°. Etter avsluttet tildrypning vidererores i 30 minutter ved 0°. Deretter fjernes kjolebadet, og opplosningen av det erholdte [2-(2-metoksy-benzamido-etyl)-fenylsulfonyl]-aziridin tilsettes 100 ml n-propylamin. Temperaturen stiger til 40 - 50°\ Reaksjonsblandingen rores videre i 1 time og deretter avdestilleres det overskytende amin i rotasjonsfordamper. Krystallgroten, som ved siden av koksalt inneholder det onskede N^-[p-[2-(2-metoksy-benz amido)-etyl] - f eny 1 su lf onyl] -N2-n-propyl- etyl end i amin , opploses i 56 ml -2-n natronlut og under roring tilsettes porsjonsvis 10,6 g bromcyan, idet man ikke lar temperaturen stige over 40°. Etter 1 time ekstraheres den erholdte substans med metylenklorid, vaskes med 20 ml 2-n natronlut og to ganger med 100 ml vann. Etter torking og inndampning av metylenkloridopplosningen omkrystalliseres resten fra eddikester og gir l-[p-[2-(2-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidinet, med smp. 144 - 147°. 28 ml of 4-n caustic soda and 4.3 g of ethyleneimine are cooled to -10 . A suspension of 35.5 g of p-[2-(2-methoxy-benzamido)-ethyl]-phenylsulfochloride in 100 ml of acetone is then added while stirring and cooling, so that the temperature does not rise above 0°. After completion of the addition, stirring continues for 30 minutes at 0°. The dressing bath is then removed, and the solution of the obtained [2-(2-methoxy-benzamido-ethyl)-phenylsulfonyl]-aziridine is added to 100 ml of n-propylamine. The temperature rises to 40 - 50°\ The reaction mixture is further stirred for 1 hour and then the excess amine is distilled off in a rotary evaporator. The crystal grain, which, in addition to common salt, contains the desired N^-[p-[2-(2-methoxy-benzamido)-ethyl]-phenyl-1-sulfonyl]-N2-n-propyl-ethyl end in amine, dissolve in 56 ml -2-n caustic soda and, while stirring, add 10.6 g of cyanogen bromide in portions, not allowing the temperature to rise above 40°. After 1 hour, the substance obtained is extracted with methylene chloride, washed with 20 ml of 2-N caustic soda and twice with 100 ml of water. After drying and evaporating the methylene chloride solution, the residue is recrystallized from ethyl acetate to give the l-[p-[2-(2-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine, with m.p. 144 - 147°.

På analog måte oppnår man fra 4,3 g etylenimin og: In an analogous way, one obtains from 4.3 g of ethyleneimine and:

100 ml isopropylamin og 26,2 g p-( 2-acetamido-etyl)-f enylsulf o-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-isopro-pyl-imidazo 1 idinet, smp. 133 - 135°', 100 ml of isopropylamine and 26.2 g of p-(2-acetamido-ethyl)-phenylsulfonyl chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazo 1 idine, m.p. 133 - 135°',

100 ml isopropylamin og 27,6 g p-(propionamido-etyl)-fenylsulfo-klorid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, smp. 111 - 112°; 100 ml of isopropylamine and 27.6 g of p-(propionamido-ethyl)-phenylsulfo-chloride 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine, m.p. 111 - 112°;

100 ml isopropylamin og 29 g p-(2-butyramido-etyl)-fenylsulfo-klorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-iso-propyl-imidazolidinet, smp. 139 - 140°; 100 ml of isopropylamine and 29 g of p-(2-butyramido-ethyl)-phenylsulfo-chloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-iso-propyl-imidazolidine, m.p. 139 - 140°;

100 ml butylamin og 26,2 g p-(2-acetamido-etyl)-fenylsulfo-klorid l-[p-(2-acetamido~etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 130 - 131°; 100 ml of butylamine and 26.2 g of p-(2-acetamido-ethyl)-phenylsulfo-chloride 1-[p-(2-acetamido~ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 130 - 131°;

100 ml butylamin og 30,6 g [ 2-( oc-metyl-butyramido) - etyl] - f enyl-sulfoklorid l-[p-[2-(a-metylbutyramido)-etyl]-fenylsulfonyl]-2-imino-3-n-butyl-imidazolidinet, smp. 114 - 116°; 100 ml of butylamine and 30.6 g [2-(α-methyl-butyramido)-ethyl]-phenyl-sulfochloride l-[p-[2-(α-methylbutyramido)-ethyl]-phenylsulfonyl]-2-imino- 3-n-butyl-imidazolidine, m.p. 114 - 116°;

100 ml butylamin og 30,6 g p-(2-valeramido-etyl)-fenylsulfo-klorid 1-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 130°; 100 ml of butylamine and 30.6 g of p-(2-valeramido-ethyl)-phenylsulfo-chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 130°;

100 ml isobutylamin og 30,6 g p-(2-valeramido-etyl)-fenylsulfo-klorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-isobu- 100 ml of isobutylamine and 30.6 g of p-(2-valeramido-ethyl)-phenylsulfo-chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-isobu-

tyl-imidazolidinet, smp. 137 - 140°; the tyl-imidazolidine, m.p. 137 - 140°;

100 ml isobutylamin og 38,9 g p-[2-(2-metoksy-o-klor-benzamido)-etyl]-fenylsulfoklorid l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 100 ml of isobutylamine and 38.9 g of p-[2-(2-methoxy-o-chloro-benzamido)-ethyl]-phenylsulfochloride l-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl ]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p.

117 - 119°; 117 - 119°;

100 ml isobutylamin og 33,0 g p-(2-cykloheksan-karboksamido-etyl)-fenylsulfoklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 175 - 177°; 100 ml of isobutylamine and 33.0 g of p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfochloride 1-[p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. . 175 - 177°;

100 ml sek.butylamin og 26,2 g p-(2-acetamido-etyl)-fenylsulfo-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-sek. butyl-imidazolidinet, smp. 106 - 108°; 100 ml sec.butylamine and 26.2 g p-(2-acetamido-ethyl)-phenylsulfo-chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-sec. butyl-imidazolidine, m.p. 106 - 108°;

100 ml sek.butylamin og 27,6 g p-(2-propionamido-etyl)-fenyl-sulfoklorid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 100 ml sec.butylamine and 27.6 g p-(2-propionamido-ethyl)-phenyl-sulfochloride 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine , m.p.

100 ml sek.butylamin og 29,0 g p-(2-butyramido-etyl)-fenylsulfo-klorid I-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-sek. butyl-imidazolidinet, smp. 100 ml sec.butylamine and 29.0 g p-(2-butyramido-ethyl)-phenylsulfo-chloride I-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-sec. butyl-imidazolidine, m.p.

100 ml tert.butylamin og 26,2 g p-(2-acetamido-etyl)-fenylsulfo-klorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-tert. butyl-imidazolidinet, smp. 127 - 128°; 100 ml tert.butylamine and 26.2 g p-(2-acetamido-ethyl)-phenylsulfo-chloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-tert. butyl-imidazolidine, m.p. 127 - 128°;

100 ml tert.butylamin og 27,6 g p-(2-propionamido-etyl)-fenyl-sulfoklorid 1-[p-(2-propionamido-etyl)-fenylsulfoklorid l-[p-(2-propionamido-etyl)-f enylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 150 - 152°. 100 ml tert.butylamine and 27.6 g p-(2-propionamido-ethyl)-phenyl-sulfochloride 1-[p-(2-propionamido-ethyl)-phenylsulfochloride l-[p-(2-propionamido-ethyl)- phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 150 - 152°.

EKSEMPEL 37- EXAMPLE 37-

28 ml 4-n natronlut og 4,3 g etylenimin avkjoles til -10 . Derpå tilsettes en suspensjon av 29,0 g p-C2-butyrylamido-etyl)- fenylsulfoklorid i 100 ml aceton under roring og avkjoling, slik at temperaturen ikke stiger over 0°. Etter avsluttet tildryp ning vidererores i 30 minutter ved 0°. Deretter fjernes kjolebadet, og opplosningen av det erholdte l-[p-(2-butyramido-etyl)-fenylsulfonyl]-aziridin tilsettes 100 ml tert.butylamin. Temperaturen stiger til 40 - 50°. Reaksjonsblandingen rores videre i 1 time og deretter avdestilleres det overskytende amin i rotasjonsfordamper. Krystallgrdten, som ved siden av koksalt inneholder det onskede N-,-[ p-( 2-butyramido-etyl)-f enylsulf onyl] - N2~tert.butyl-etylendiamin, opploses i 56 ml 2-n natronlut og under roring tilsettes porsjonsvis 10,6 g bromcyan, idet man ikke lar temperaturen stige over 40°. Etter 1 time ekstraheres den erholdte substans med metylenklorid, vaskes med 20 ml 2-n natronlut og to ganger med 100 ml vann. Etter torking og inndampning av metylenkloridoppldsningen omkrystalliseres resten fra eddikester og gir l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet med smp. 148 - 149°. 28 ml of 4-n caustic soda and 4.3 g of ethyleneimine are cooled to -10 . A suspension of 29.0 g of p-C2-butyrylamido-ethyl)- phenylsulfochloride in 100 ml of acetone while stirring and cooling, so that the temperature does not rise above 0°. After finishing the infusion ning is further stirred for 30 minutes at 0°. The dressing bath is then removed, and the solution of the obtained 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-aziridine is added to 100 ml of tert-butylamine. The temperature rises to 40 - 50°. The reaction mixture is further stirred for 1 hour and then the excess amine is distilled off in a rotary evaporator. The crystal paste, which contains the desired N-,-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N2-tert.butyl-ethylenediamine in addition to sodium chloride, is dissolved in 56 ml of 2-n caustic soda and, while stirring, is added 10.6 g of cyanogen bromide in portions, the temperature not being allowed to rise above 40°. After 1 hour, the substance obtained is extracted with methylene chloride, washed with 20 ml of 2-N caustic soda and twice with 100 ml of water. After drying and evaporating the methylene chloride solution, the residue is recrystallized from ethyl acetate to give 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine with m.p. 148 - 149°.

100 ml tert.butylamin og 30,6 g p-(2-isovaleramido-etyl)-fenylsulfoklorid l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 152 - 154°; 100 ml tert.butylamine and 30.6 g p-(2-isovaleramido-ethyl)-phenylsulfochloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. . 152 - 154°;

100 ml tert.butylamin og 35,5 g p-[2-(2-metoksybenzamido)-etyl]-fenylsulfoklorid l-[p-[2-(2-metoksybenzamido)-etyl]-fenylsulfo-nyl] -2-imino-3-tert.butyl-imidazolidinet, smp. 134 - 136°; 100 ml tert.butylamine and 35.5 g p-[2-(2-methoxybenzamido)-ethyl]-phenylsulfochloride 1-[p-[2-(2-methoxybenzamido)-ethyl]-phenylsulfonyl]-2-imino -3-tert.butyl-imidazolidine, m.p. 134 - 136°;

100 ml tert.butylamin og 39,0 g p-[2-(2-metoksy-5-klor-benzamido) -etyl]-fenylsulfoklorid l-[p-[2-(2-metoksy-5-klorbenz-amido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 124 - 126°; 100 ml of tert-butylamine and 39.0 g of p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfochloride l-[p-[2-(2-methoxy-5-chloro-benzamido) -ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 124 - 126°;

100 ml cyklopentylamin og 30,6 g p-(2-valeramido-etyl)-fenyl-sulfoklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 132 - 134°; 100 ml of cyclopentylamine and 30.6 g of p-(2-valeramido-ethyl)-phenyl-sulfochloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 132 - 134°;

100 ml cyklopentylamin og 29,0 g p-(2-butyramido-etyl)-fenyl-sulfoklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 100 ml of cyclopentylamine and 29.0 g of p-(2-butyramido-ethyl)-phenyl-sulfochloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p.

100 ml cyklopentylamin og 33,0 g p-(2-cykloheksan-karboksamido- 100 ml of cyclopentylamine and 33.0 g of p-(2-cyclohexane-carboxamido-

etyl)-fenylsulfoklorid l-[p-(2-cykloheksan-kårboksamido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. ethyl)-phenylsulfochloride 1-[p-(2-cyclohexane-corboxamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p.

178 - 179°; 178 - 179°;

100 ml cykloheksylamin og 24,8 g p-(2-formamido-etyl)-fenylsul-foklorid l-[p-(2-formamido-etyl)-f enylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 135 - 136°; 100 ml of cyclohexylamine and 24.8 g of p-(2-formamido-ethyl)-phenylsulfochloride 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 135 - 136°;

100 ml cykloheksylamin og 26,2 g p-(2-acetamido-etyl)-fenylsul-foklorid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 181 - 183°; 100 ml of cyclohexylamine and 26.2 g of p-(2-acetamido-ethyl)-phenylsulfochloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 181 - 183°;

100 ml cykloheksylamin og 29,0 g p-[ 2-(N-rnetylacetamido) - propyl]-fenylsulfoklorid l-[p-[2-(N-metyl-acetamido)-propyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 100 ml of cyclohexylamine and 29.0 g of p-[2-(N-methylacetamido)-propyl]-phenylsulfochloride 1-[p-[2-(N-methyl-acetamido)-propyl]-phenylsulfonyl]-2-imino-3 -cyclohexyl-imidazolidine, m.p.

108 - 110°; 108 - 110°;

100 ml cykloheksylamin og 27,6 g p-(2-propionamido-etyl)-fenyl-sulfoklorid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet " 1/2 F^O, smp. 110 - 112°; 100 ml cyclohexylamine and 27.6 g p-(2-propionamido-ethyl)-phenyl-sulfochloride 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine " 1/2 F^O, mp 110 - 112°;

100 ml cykloheksylamin og 29,0 g p-(2-butyramido-etyl)-fenyl-sulf ok lorid l-[p-(2-butyramido-etyl)- f enylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet * 1/2 F^O, smp. 143 - 144°; 100 ml cyclohexylamine and 29.0 g p-(2-butyramido-ethyl)-phenyl-sulfo chloride l-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine * 1/2 F^O, m.p. 143 - 144°;

100 ml cykloheksylamin og 30,4 g p-(2-valeramido-etyl)-fenylsu1-foklorid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet • 1/4 F^O, smp. 154 - 155°; 100 ml cyclohexylamine and 30.4 g p-(2-valeramido-ethyl)-phenylsulfonyl chloride 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine • 1/4 F^O, m.p. 154 - 155°;

100 ml cykloheksylamin og 30,4 g p-(2-isova1eramido-etyl)-fenylsulfoklorid l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 180 - 181°; 100 ml of cyclohexylamine and 30.4 g of p-(2-isovaleramido-ethyl)-phenylsulfochloride 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 180 - 181°;

100 ml cykloheksylamin og 35,4 g p-[2-(2-metoksy-benzamido)-etyl]-fenylsulfoklorid l-[p-[2-(2-metoksy-benzamido)- etyl]- 100 ml cyclohexylamine and 35.4 g p-[2-(2-methoxy-benzamido)-ethyl]-phenylsulfochloride l-[p-[2-(2-methoxy-benzamido)-ethyl]-

\ fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 105 - \phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 105 -

107°; 107°;

100 ml cykloheksylamin og 33,0 g p-(2-cykloheksyl-karboksamido-etyl)-fenylsulfoklorid l-[p-(2-cykloheksyl-karboksamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 167 - 168°; 100 ml cyclohexylamine and 33.0 g p-(2-cyclohexyl-carboxamido-ethyl)-phenylsulfochloride 1-[p-(2-cyclohexyl-carboxamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. . 167 - 168°;

100 ml cykloheptylamin og 26,2 g p-(2-acetamido-etyl)-fenyl-sulfoklorid l-[p-(2-acetamido-etyl)-f enylsulfonyl]-2-Imino-3-cykloheptyl-imidazolidinet, smp. 166 - 167°; 100 ml of cycloheptylamine and 26.2 g of p-(2-acetamido-ethyl)-phenyl-sulfochloride 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-Imino-3-cycloheptyl-imidazolidine, m.p. 166 - 167°;

100 ml cykloheptylamin og 29,0 g p-(2-butyramido-etyl)-fenyl-sulfoklorid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 100 ml of cycloheptylamine and 29.0 g of p-(2-butyramido-ethyl)-phenyl-sulfochloride 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p.

EKSEMPEL 38 EXAMPLE 38

28 ml 4-n natronlut og 5,7 g propylenimin avkjoles til -10°. 28 ml of 4-n caustic soda and 5.7 g of propyleneimine are cooled to -10°.

Derpå tilsettes en suspensjon av 29,0 g p-(2-butyramidoetyl)-fenylsulfoklorid i 100 ml aceton under roring og avkjoling, slik at temperaturen ikke stiger over 0°. Etter avsluttet tildrypning vidererores i 30 minutter ved 0°. Deretter fjernes kjolebadet,'og opplosningen av det erholdte l-[p-(2-butyramido-etyl) -f enylsulfonyl]-2-metyl-aziridin tilsettes 100 ml cykloheksylamin. Temperaturen stiger til 40 - 50°. Reaksjonsblandingen rores videre i 1 time og deretter avdestilleres det overskytende amin i rotasjonsfordamper. Krystallgroten, som ved siden av koksaltet inneholder det onskede 2-[p-(2-butyramido -et yl)-f en ylsulfonyl]-l-cyk loheksylamino-propan, opploses i 56 ml 2-n natronlut og tilsettes under roring porsjonsvis 10,6 g bromcyan, idet man ikke lar temperaturen stige over 40°. Etter 1 time ekstraheres den erholdte substans med metylen-klorid, vaskes med 20 ml 2-n natronlut og to ganger med 100 ml vann. Etter torking og inndampning av metylenkloridopplbsningen omkrystalliseres resten fra eddikester og gir l-[p-(2-acetamido-etyl) -f enylsulfonyl ] -2- imino -3-cykloh ek syl-5 -met yl- imidazolidinet med smp. 109 - 111°. A suspension of 29.0 g of p-(2-butyramidoethyl)-phenylsulfochloride in 100 ml of acetone is then added while stirring and cooling, so that the temperature does not rise above 0°. After completion of the addition, stirring continues for 30 minutes at 0°. The dressing bath is then removed, and the solution of the obtained 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-methyl-aziridine is added to 100 ml of cyclohexylamine. The temperature rises to 40 - 50°. The reaction mixture is further stirred for 1 hour and then the excess amine is distilled off in a rotary evaporator. The crystal grain, which contains the desired 2-[p-(2-butyramido-ethyl)-phenylsulfonyl]-1-cyclohexylamino-propane in addition to the sodium hydroxide solution, is dissolved in 56 ml of 2-n caustic soda and added with stirring in portions 10 .6 g of cyanogen bromide, not allowing the temperature to rise above 40°. After 1 hour, the substance obtained is extracted with methylene chloride, washed with 20 ml of 2-N caustic soda and twice with 100 ml of water. After drying and evaporating the methylene chloride solution, the residue is recrystallized from ethyl acetate to give l-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-5-methyl-imidazolidine with m.p. 109 - 111°.

EKSEMPEL 39 EXAMPLE 39

28 ml 4-n natronlut og 5,7 g propylenimin avkjoles til -10°. Derpå tilsettes en suspensjon av 26,2 g p-(2-acetamido-etyl)- 28 ml of 4-n caustic soda and 5.7 g of propyleneimine are cooled to -10°. A suspension of 26.2 g of p-(2-acetamido-ethyl)-

fenylsulfoklorid i 100 ml aceton under roring og avkjoling, phenylsulfochloride in 100 ml of acetone while stirring and cooling,

slik at temperaturen ikke stiger over 0°. Etter avsluttet tildrypning vidererores i 30 minutter ved 0°. Deretter fjernes kjolebadet og opplosningen av det erholdte l-[p-(2-acetamido-etyl)-f enylsulf onyl]-2-n^etyl-aziridin tilsettes 100 ml n-butylamin. Temperaturen stiger til 40 - 50°. Reaksjonsblandingen rores videre i 1 time og deretter avdestilleres det overskyt- so that the temperature does not rise above 0°. After completion of the addition, stirring continues for 30 minutes at 0°. Then the dressing bath is removed and the solution of the obtained 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-n^ethyl-aziridine is added to 100 ml of n-butylamine. The temperature rises to 40 - 50°. The reaction mixture is stirred further for 1 hour and then the excess is distilled off

ende amin i rotasjonsfordamper. Krystallgrbten, som ved siden av koksalt inneholder det onskede 2-[p-(2-acetamido-etyl)-fenylsulfonyl]-1-n-butylamino-propan, opplbses i 56 ml 2-n natronlut og tilsettes under roring porsjonsvis 10,6 g bromcyan, idet man ikke lar temperaturen stige over 40°. Etter 1 time ekstraheres den erholdte substans med metylenklorid, end amine in rotary evaporator. The crystal grain, which contains the desired 2-[p-(2-acetamido-ethyl)-phenylsulfonyl]-1-n-butylamino-propane in addition to sodium chloride, is dissolved in 56 ml of 2-n caustic soda and added, while stirring, in portions 10.6 g of cyanogen bromide, not allowing the temperature to rise above 40°. After 1 hour, the substance obtained is extracted with methylene chloride,

vaskes med 20 ml 2-n natronlut og to ganger med 100 ml vann. washed with 20 ml of 2-n caustic soda and twice with 100 ml of water.

Etter tbrking og inndampning av metylenkloridopplbsningen omkrystalliseres resten fra eddikester og gir l-[p-(2-acetamido-etyl )- fenylsu 1fonyl]-2 -imino-3-n-butyl-5-metyl-imidazolidinet med smp. 98 - 99°. After concentrating and evaporating the methylene chloride solution, the residue is recrystallized from ethyl acetate to give 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-n-butyl-5-methyl-imidazolidine with m.p. 98 - 99°.

EKSEMPEL 40 EXAMPLE 40

Til en blanding av 4 g natriumhydroksyd, 15 ml vann og 300 ml dimetylsulfoksyd opplbser man 28,4 g p-(2-isovaleramido-etyl)-benzensulfonamid og 16 g N-(2-klor-etyl)-N-buty 1-cyanamid. Den erholdte opplosning koker man i 1 time ved tilbakelbp (badtemperatur: 110°). Dimetylsulfoksydet avdestilleres, så i vakuum, To a mixture of 4 g of sodium hydroxide, 15 ml of water and 300 ml of dimethylsulfoxide, 28.4 g of p-(2-isovaleramido-ethyl)-benzenesulfonamide and 16 g of N-(2-chloro-ethyl)-N-butyl 1- cyanamide. The obtained solution is boiled for 1 hour at reflux (bath temperature: 110°). The dimethylsulfoxide is distilled off, then in a vacuum,

og resten, en brun olje, opptas i metylenklorid. Man vasker tre ganger med vann, tbrker og filtrerer den organiske fase, and the residue, a brown oil, is taken up in methylene chloride. Wash three times with water, wash and filter the organic phase,

som etter inndampning gir brune krystaller. Etter krystallisa-sjon fra eddikester oppnår man l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet med smp. 130 - 130,5°. which after evaporation gives brown crystals. After crystallization from acetic ester, 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-2-imino-3-butyl-imidazolidine is obtained with m.p. 130 - 130.5°.

På analog måte oppnår man fra: Analogously, one obtains from:

14,7 g N-(2-klor-etyl)-N-propyl-cyanamid og 27,0 g p-(2-butyramido-etyl)-benzensulfonamid l-[p-(2-butyramido-etyl)-fenyl-sulfonyl]-2-imino-3-propyl-imidazolidinet, smp. 114 - 116°; 14.7 g of N-(2-chloro-ethyl)-N-propyl-cyanamide and 27.0 g of p-(2-butyramido-ethyl)-benzenesulfonamide l-[p-(2-butyramido-ethyl)-phenyl- sulfonyl]-2-imino-3-propyl-imidazolidine, m.p. 114 - 116°;

14,7 g N-(2-k,lor-etyl)-N-propyl-cyanamid og 33,4 g p-[2-(3-rne tok sy-benzamido )-etyl]-benzensulfonamid l-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-propyl-imidazolidinet, smp. 144 - 147°; 14.7 g of N-(2-chloro-ethyl)-N-propyl-cyanamide and 33.4 g of p-[2-(3-retok sy-benzamido)-ethyl]-benzenesulfonamide l-[p- [2-(3-Methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-propyl-imidazolidine, m.p. 144 - 147°;

14,7 g ,N-(2-klor-etyl)-N-isopropyl-cyariamid og 25,6 g p-(2-propionamido-etyl)-benzensulfonamid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, smp. 111 - 112°-, 14.7 g of ,N-(2-chloro-ethyl)-N-isopropyl-cyariamide and 25.6 g of p-(2-propionamido-ethyl)-benzenesulfonamide 1-[p-(2-propionamido-ethyl)-phenylsulfonyl ]-2-imino-3-isopropyl-imidazolidine, m.p. 111 - 112°-,

14,7 g N-(2-klor-etyl)-N-isopropyl-cyanamid og 27,0 g p-(2-butyramido-etyl)-benzensulfonamid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, smp. 139 - 140°; 14.7 g of N-(2-chloro-ethyl)-N-isopropyl-cyanamide and 27.0 g of p-(2-butyramido-ethyl)-benzenesulfonamide l-[p-(2-butyramido-ethyl)-phenylsulfonyl] -2-imino-3-isopropyl-imidazolidine, m.p. 139 - 140°;

16,0 g N-(2-kloretyl)-N-butyl-cyanamid og 24,2 g p-(2-acetamido-etyl) -benzensulfonamid l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 130 -. 131°; 16.0 g of N-(2-chloroethyl)-N-butyl-cyanamide and 24.2 g of p-(2-acetamido-ethyl)-benzenesulfonamide l-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2 -imino-3-butyl-imidazolidine, m.p. 130 -. 131°;

16,0 g N-(2-kloretyl)-N-butyl-cyanamid og 28,4 g p-(2-metyl-butyramido- etyl)-benzensulfonamid l-[p-[2-(2-metyl-butyramido)-etyl]-fenylsulfonyl]-2- imino-3'-bu tyl - imidazolidinet, smp. 16.0 g N-(2-chloroethyl)-N-butyl-cyanamide and 28.4 g p-(2-methyl-butyramido-ethyl)-benzenesulfonamide l-[p-[2-(2-methyl-butyramido) -ethyl]-phenylsulfonyl]-2-imino-3'-butyl-imidazolidine, m.p.

114 - 116°; 114 - 116°;

16,0 g N-(2-kloretyl)-N-butyl-cyanamid og 28,4 g p-(2-valeramido-etyl)-benzensulfonamid l-[p-(2-valeramido-etyl)-fenyl-sulfonyl] -2- imino-3-butyl-imidazolidinet , smp-. 130°; 16.0 g of N-(2-chloroethyl)-N-butyl-cyanamide and 28.4 g of p-(2-valeramido-ethyl)-benzenesulfonamide l-[p-(2-valeramido-ethyl)-phenyl-sulfonyl] -2-imino-3-butyl-imidazolidine, m.p. 130°;

16,0 g N-(2-kloretyl)-N-butyl-cyanamid og 33,9 g p-[2-(2-klorbenzamido)-etyl]-benzensulfonamid l-[p-[2-(2-klorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 155 - 157°; 16.0 g of N-(2-chloroethyl)-N-butyl-cyanamide and 33.9 g of p-[2-(2-chlorobenzamido)-ethyl]-benzenesulfonamide l-[p-[2-(2-chlorobenzamido) -ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 155 - 157°;

16,0 g N-(2-kloretyl)-N-butyl-cyanamid og 37,2 g p-[l-(a,a,a-trifluor-m-toluyl-amido)-etyl] -benz ensulf on amid l-[p-(a,oc,a-trifluor-m-toluyl-amido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet som olje; 16.0 g of N-(2-chloroethyl)-N-butyl-cyanamide and 37.2 g of p-[1-(a,a,a-trifluoro-m-toluyl-amido)-ethyl]-benz ensulfonamide 1-[p-(α,oc,α-trifluoro-m-toluyl-amido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine as an oil;

16,0 g N-(2-kloretyl)-N-isobutyl-cyanamid og 28,4 g p-(2-valeramido-etyl)-benzensulfonamid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 130°;. 16.0 g N-(2-chloroethyl)-N-isobutyl-cyanamide and 28.4 g p-(2-valeramido-ethyl)-benzenesulfonamide 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2 -imino-3-isobutyl-imidazolidine, m.p. 130°;.

16,0 g N-(2-kloretyl)-N-isobutyl-cyanamid og 36,9 g p-[2-(2-metoksy-5--klorbenzamido)-etyl]-benzensulfonamid l-[p-[2-(2-metoksy-b-klorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 117 - 119°; 16.0 g of N-(2-chloroethyl)-N-isobutyl-cyanamide and 36.9 g of p-[2-(2-methoxy-5-chlorobenzamido)-ethyl]-benzenesulfonamide l-[p-[2- (2-methoxy-b-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 117 - 119°;

16,0 g N-(2-kloretyl)-N-isobutyl-cyanamid og 30,9 g p-(2-cykloheksan-kårboksamido-etyl)-benzensulfonamid l-[p-(2-cykloheksan-kårbok samido)-etyl]-fenylsulfonyl]-2-imLno-3-Ls6butyl-imidazolidinet smp. 17b - 177°; 16.0 g of N-(2-chloroethyl)-N-isobutyl-cyanamide and 30.9 g of p-(2-cyclohexane-corboxamido-ethyl)-benzenesulfonamide 1-[p-(2-cyclohexane-corboxamido)-ethyl ]-phenylsulfonyl]-2-imLno-3-Ls6butyl-imidazolidine m.p. 17b - 177°;

16,0 g N-(2-kloretyl)-N-sek.butyl-cyanamid og 24,2 g p-(2-acetamido-etyl)-benzensulfonamid l-[p-(2-acetarnido-etyl)-fenylsul fonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 106 - 108°; 16.0 g N-(2-chloroethyl)-N-sec.butyl-cyanamide and 24.2 g p-(2-acetamido-ethyl)-benzenesulfonamide 1-[p-(2-acetarnido-ethyl)-phenylsulfonyl ]-2-imino-3-sec.butyl-imidazolidine, m.p. 106 - 108°;

16,0 g N-(2-kloretyl)-N-sek.bu tyl-cyanamid og 2b,6 g p-(2-propionamido-etyl)-benzensulfonamid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 16.0 g N-(2-chloroethyl)-N-sec.butyl-cyanamide and 2b.6 g p-(2-propionamido-ethyl)-benzenesulfonamide 1-[p-(2-propionamido-ethyl)-phenylsulfonyl ]-2-imino-3-sec.butyl-imidazolidine, m.p.

16,0 ,g N-(2-kloretyl)-N-sek.butyl-cyanamid og 27,0 g p-(2-bu tyramido-etyl)-benzensul fonamid l-[p-(2-bu tyramido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet,. smp. 16.0 g N-(2-chloroethyl)-N-sec.butyl-cyanamide and 27.0 g p-(2-bu tyramido-ethyl)-benzenesulfonamide 1-[p-(2-bu tyramido-ethyl) )-phenylsulfonyl]-2-imino-3-sec.butyl-imidazolidine,. m.p.

,16,0 g N-(2-kloretyiy-N-tert.butyl-cyanamid og 24,2 g p-(2-acetamido-etyl)-benzensulfonamid l-[p-(2-acetamido-ety1)-benzensulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 127 - 128°; ,16.0 g N-(2-chloroethyl-N-tert.butyl-cyanamide and 24.2 g p-(2-acetamido-ethyl)-benzenesulfonamide 1-[p-(2-acetamido-ethyl)-benzenesulfonyl] -2-imino-3-tert-butyl-imidazolidine, mp 127 - 128°;

16,0 g N-(2-kIoretyl)-N-tert.butyl-cyanamid og 27,0 g p-(2-butyramido-etyl)-benzensulfonamid l-[p-(2-butyramido-etyl)-f enylsulfonyl}-2-imino-3-tert.butyl-imidazolidinet, smp. 16.0 g of N-(2-chloroethyl)-N-tert.butyl-cyanamide and 27.0 g of p-(2-butyramido-ethyl)-benzenesulfonamide 1-[p-(2-butyramido-ethyl)-phenylsulfonyl }-2-imino-3-tert.butyl-imidazolidine, m.p.

148 - 149°. 148 - 149°.

EKSEMPEL 41 EXAMPLE 41

Til en blanding av 4 g natriumhydroksyd, 15 ml vann og 300 ml dimetylsulfoksyd oppldser man 28,4 g p-(2-isovaleramido-etyl)-benzensulfonamid og 16 g N-(2-klor-etyl)-N-tert.butyl-cyanamid. Den erholdte opplosning koker man i 1 time ved tilbakelop (badtemperatur: 110°). Dimetylsulfoksydet avdestilleres så i vakuum, og resten, en "brun olje, opptas i metylenklorid. Man vasker tre ganger med vann, tdrker og filtrerer den organiske fase, som gir etter inndampning brune krystaller. Etter kry-stallisasjon fra eddikester oppnår man l-[p-(2-isovaleramido-etyl)-benzensul fonyl]-2-imino-3-tert.butyl-imidazolidinet med smp. 152 - 154°. To a mixture of 4 g of sodium hydroxide, 15 ml of water and 300 ml of dimethylsulfoxide, 28.4 g of p-(2-isovaleramido-ethyl)-benzenesulfonamide and 16 g of N-(2-chloro-ethyl)-N-tert-butyl are dissolved -cyanamide. The obtained solution is boiled for 1 hour at reflux (bath temperature: 110°). The dimethyl sulfoxide is then distilled off in a vacuum, and the residue, a brown oil, is taken up in methylene chloride. The organic phase is washed three times with water, dried and filtered, which after evaporation gives brown crystals. After crystallization from acetic acid, l-[ The p-(2-isovaleramido-ethyl)-benzenesulfonyl]-2-imino-3-tert-butyl-imidazolidine with mp 152-154°.

På analog måte oppnår man fra: Analogously, one obtains from:

16,0 g N-(2-kloretyl)-N-tert.butyl-cyanamid og 31,8 g p-[2-(2-'. toluylamido)-etyl]-benzensulfonamid l-[p-[2-(2-toluylamido)-etyl]-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 160 - 161° 16.0 g of N-(2-chloroethyl)-N-tert.butyl-cyanamide and 31.8 g of p-[2-(2-'.toluylamido)-ethyl]-benzenesulfonamide l-[p-[2-( 2-toluylamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 160 - 161°

16,0 g N-(2-kloretyl)-N-tert.butyl-cyanamid og 33,8 g p-[2-(2-klor-benzamido)-etyl]-benzensulfonamid l-[p-[2-(2-klor-benzamido ) -etyl] -f enylsulfonyl] -2- imino -3-tert. butyl-imidazolidinet, smp. 152 - 154°; 16.0 g of N-(2-chloroethyl)-N-tert.butyl-cyanamide and 33.8 g of p-[2-(2-chloro-benzamido)-ethyl]-benzenesulfonamide l-[p-[2-( 2-Chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert. butyl-imidazolidine, m.p. 152 - 154°;

16,0 g N-(2-kloretyl)-N-tert.butyl-cyanamid og 39,6 g p-[2-( 3 ,4',5-trImetoksy-benzamido) - etyl]-benzensul f onamid l-[p-[2-(3,4,5-trimetoksy-benzamido)-etyl]-fenylsu lfonylJ-2 -imino-3-tert.butyl-imidazolidinet, smp. 130 - 132°; 16.0 g of N-(2-chloroethyl)-N-tert.butyl-cyanamide and 39.6 g of p-[2-(3,4',5-trimethoxy-benzamido)-ethyl]-benzenesulfonamide l- [p-[2-(3,4,5-trimethoxy-benzamido)-ethyl]-phenylsulfonyl-2-imino-3-tert.butyl-imidazolidine, m.p. 130 - 132°;

16,0 g N-(2-kloretyl)-N-tert..butyl-cyanamid og 25,6 g p-(3-acetamido-propyl)-benzensulfonamid 1-[p-(3-acetamido-propyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 106 - 108°; 16.0 g N-(2-chloroethyl)-N-tert.butyl-cyanamide and 25.6 g p-(3-acetamido-propyl)-benzenesulfonamide 1-[p-(3-acetamido-propyl)-phenylsulfonyl ]-2-imino-3-tert.butyl-imidazolidine, m.p. 106 - 108°;

16,0 g N-(2-kloretyl)-N-tert.butyl-cyanamid og 33,8 g p-[l-(2-klorbenzamido) - etyl] - benzensulf onamid l-[ p-[ 1- ( 2-klorbenzamido)-etyl]-f enylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, 16.0 g N-(2-chloroethyl)-N-tert.butyl-cyanamide and 33.8 g p-[l-(2-chlorobenzamido)-ethyl]-benzenesulfonamide l-[ p-[ 1-( 2 -chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert-butyl-imidazolidine,

smp. 166 - 168°; m.p. 166 - 168°;

17,4 g N-(2-kloretyl)-N-cyklopentyl-cyanamid og 27,0 g p-(2-butyramido-etyl)-benzensul fonamid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 17.4 g of N-(2-chloroethyl)-N-cyclopentyl-cyanamide and 27.0 g of p-(2-butyramido-ethyl)-benzenesulfonamide l-[p-(2-butyramido-ethyl)-phenylsulfonyl]- The 2-imino-3-cyclopentyl-imidazolidine, m.p.

17,4 g N-(2-kloretyl)-N-cyklopentyl-cyanamid og 28,4 g p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 132 - 134°; 17.4 g of N-(2-chloroethyl)-N-cyclopentyl-cyanamide and 28.4 g of p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine, m.p. 132 - 134°;

17,4 g N-(2-kloretyl)-N-cyklopentyl-cyanamid og 30,9 g p-(2-cykloheksan-kårboksamido-etyl)-benzensulfonamid l-[p-(2-cykloheksan-kårboksamido-e tyl)-f enylsulfonyl]-2-imino-3-cyklopen tyl-imidazolidinet, smp. 178 - 179°; 17.4 g of N-(2-chloroethyl)-N-cyclopentyl-cyanamide and 30.9 g of p-(2-cyclohexane-corboxamido-ethyl)-benzenesulfonamide 1-[p-(2-cyclohexane-corboxamido-ethyl) -phenylsulfonyl]-2-imino-3-cyclopenyl-imidazolidine, m.p. 178 - 179°;

18,8 g N-(2-kloretyl)-N-cykloheksyl-cyanamid og 22,8 g p-(2-f ormamido-etyl)- ben z ensulfonamid 1-[p-(2-formamido-e tyl)-fenylsulfonyl]-2-imino-3-cyk1ohek syl-imida zolid inet, smp. 18.8 g N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 22.8 g p-(2-formamido-ethyl)-benzenesulfonamide 1-[p-(2-formamido-ethyl)- phenylsulfonyl]-2-imino-3-cyclohexylimidazolidin, m.p.

135 - 136°; 135 - 136°;

18,8 g N-(2-kloretyl)-N-cykloheksyl-cyanamid og 24,2 g p-(2-acetamido-etyl)-benzensulfonamid 1-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 24.2 g of p-(2-acetamido-ethyl)-benzenesulfonamide 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2 -imino-3-cyclohexyl-imidazolidine, m.p.

181 - 183°; 181 - 183°;

18,8 g N-(2-kloretyl)-N-cykloh'eksyl-cyanamid og 27,0 g p-[2-(N-metyl-acetamido)-propyl]-benzensulfonamid l-[p-[2-(N-metylacetamido)-propyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 108 - 110°; 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 27.0 g of p-[2-(N-methyl-acetamido)-propyl]-benzenesulfonamide l-[p-[2-( N-methylacetamido)-propyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 108 - 110°;

18,8 g N-(2-kloretyl)-N-cykloheksyl-cyanamid og 25,6 g p-(2-propionamido-etyl)-benzensulfonamid l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin • 1/2 h^O, smp. 110 - 112°;. 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 25.6 g of p-(2-propionamido-ethyl)-benzenesulfonamide 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2 -imino-3-cyclohexyl-imidazolidine • 1/2 h^O, m.p. 110 - 112°;.

18,8 g N-(2-klor-etyl)-N-cykloheksyl-cyanamid og 27,0 g p-(2-butyramido-etyl)-benzensulfonamid 1-[p-(2-butyramido-etyl)- 18.8 g N-(2-chloro-ethyl)-N-cyclohexyl-cyanamide and 27.0 g p-(2-butyramido-ethyl)-benzenesulfonamide 1-[p-(2-butyramido-ethyl)-

fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin 1/2 F^O, smp. 143 - 144°^phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine 1/2 F^O, m.p. 143 - 144°^

18,8 g N-(2-kloretyl)-N-cykloheksyl-cyanamid og 28,4 g p-(2-valeramido-etyl)-benzensulfonamid l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2 - imino-3-cykloheksy1-imidazoI idin 1/4 F^O, smp. 154 - 155°; 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 28.4 g of p-(2-valeramido-ethyl)-benzenesulfonamide 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2 - imino-3-cyclohexyl-imidazoIidine 1/4 F^O, m.p. 154 - 155°;

18,8 g N-(2-kloretyl)-N-cykloheksyl-cyanamid og 28,4 g p-(2-isoval eramido - etyl) - ben zen su 1 f onamid l-[ p-( 2- isoval eramido - e ty 1}-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 180 - 181°; 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 28.4 g of p-(2-isovaleramido-ethyl)-benzene su 1phonamide l-[p-(2-isovaleramido- e ty 1}-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, mp 180 - 181°;

18,8 g N-(2-kloretyl)-N-cykloheksyl-cyanamid og 33,9 g p-[2-(2-metoks y-ben zamido)-etyl]-benzensul fonamid l-[p-[2-(2-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazo-' lidinet, smp. 178 - 179°; 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 33.9 g of p-[2-(2-methoxy-benzamido)-ethyl]-benzenesulfonamide l-[p-[2- (2-Methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazo-' lidine, m.p. 178 - 179°;

18,8 g N-(2-kloretyl)-N-cyk.bheksyl-cyanamid og 30,9 g p-(2-cykloheksan-kårboksamido-etyl;-benzensulfonamid l-[p-(2-cyklo-heks an-kårboksamido-etyl)-fenylsuIfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 167 - 168°; 18.8 g of N-(2-chloroethyl)-N-cyclohexyl-cyanamide and 30.9 g of p-(2-cyclohexane-carboxamido-ethyl;-benzenesulfonamide 1-[p-(2-cyclohexan- carboxamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, mp 167-168°;

20,2 g N-(2-kloretyl)-N-cykloheptyl-cyanamid og 24,2 g p-(2-acet amido-etyl)- ben zen sul fon am id l-[ p-(acet am ido -etyl) - f en ylsulfonyl] -2-imino-3-cyklohepty.l-imidazolidinet, smp. 166 - 167°; 20.2 g of N-(2-chloroethyl)-N-cycloheptyl-cyanamide and 24.2 g of p-(2-acetamido-ethyl)-benzene sulfonamide l-[p-(acetamido-ethyl) ) - phenylsulfonyl]-2-imino-3-cycloheptyl.1-imidazolidine, m.p. 166 - 167°;

20,2 g N-(2-kloretyl)-N-cykloheptyl-cyanamid og .27,0 g p-(2-butyramido-etyl)-benzensulfonamid l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 20.2 g N-(2-chloroethyl)-N-cycloheptyl-cyanamide and .27.0 g p-(2-butyramido-ethyl)-benzenesulfonamide l-[p-(2-butyramido-ethyl)-phenylsulfonyl]- The 2-imino-3-cycloheptyl-imidazolidine, m.p.

EKSEMPEL 42 EXAMPLE 42

a) 38,8 g N-[ p-'( 2-propionamido-etyl)-f enylsul f onyl]-N-2-brom-etyl-cyanamid oppvarmes i 200 ml alkohol med 12 g n-propylamin a) 38.8 g of N-[p-'(2-propionamido-ethyl)-phenylsulfonyl]-N-2-bromo-ethyl-cyanamide are heated in 200 ml of alcohol with 12 g of n-propylamine

i 1 time under tilbakelop. Derpå inndampes reaksjonsblandingen på rotasjonsfordamper. Resten fortynnes med 50 ml eddikester og ekstraheres to ganger med 80 ml 2-n saltsyre. Den vandige fase for 1 hour during backflow. The reaction mixture is then evaporated on a rotary evaporator. The residue is diluted with 50 ml of acetic acid and extracted twice with 80 ml of 2-N hydrochloric acid. The aqueous phase

innstilles alkalisk med 2-n natronlut og utrystes to ganger med 100 ml metylenklorid. Metylenkloridopplosningen vaskes med vann, tdrkes og inndampes. Resten krystalliseres fra eddikester og gir det rene l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-n-propyl-imidazolidin med smp. 130 - 131°. made alkaline with 2-n sodium hydroxide solution and shaken twice with 100 ml of methylene chloride. The methylene chloride solution is washed with water, dried and evaporated. The residue is crystallized from acetic ester and gives the pure 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-n-propyl-imidazolidine with m.p. 130 - 131°.

På analog måte oppnår man fra: Analogously, one obtains from:

40,2 g N-[p-(2-butyramidbetyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 12,0 g propylamin l-[p-(2-butyramido-etyl)-fenyl-sulf onyl J -2- imino-3-propyl- imidazol idin • 1 H2O, smp. 114 - 116°; 40.2 g of N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 12.0 g of propylamine l-[p-(2-butyramido-ethyl)-phenyl-sulfonyl J - 2-imino-3-propyl-imidazolidine • 1 H2O, m.p. 114 - 116°;

46,6 g N-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfonyl]-N-2-brometyl-cyanamid og 12,0 g propylamin l-[p-[2-(3-metoksy-benzamido )- etyl] -f en ylsulfonyl] -2- im ino-3-pro py 1- imidazolidinet, smp. 144 - 147°; 46.6 g of N-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 12.0 g of propylamine l-[p-[2-(3- methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-propyl 1-imidazolidine, m.p. 144 - 147°;

38,8 g N-[p-(2-propionamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 12,0 g isopropylamin l-[p-( 2-propionamido-etyl)-fenylsulfon yl]-2-imino-3-isopropyl-imidazo1 id inet, smp. 111 - 112°; 38.8 g N-[p-(2-propionamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 12.0 g isopropylamine 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]- 2-imino-3-isopropyl-imidazo1 id inet, m.p. 111 - 112°;

40,2 g N-[p-(2-butyramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 12,0 g isopropylamin l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazolidinet, smp. 139 - 140°; 40.2 g N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 12.0 g isopropylamine 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2 -imino-3-isopropyl-imidazolidine, m.p. 139 - 140°;

37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g butylamin l-[p-(2-acetamido-etyl)-fenyl-sulf onyl]-2- imino-3-butyl-imidazolidinet,- smp. 130 - 131°; 37.4 g of N-[p-(2-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of butylamine 1-[p-(2-acetamido-ethyl)-phenyl-sulfonyl ]-2-imino-3-butyl-imidazolidine, m.p. 130 - 131°;

38,8 g N-[ p-( 2-propionamido-etyl) -f enylsulf onyl ]-N-2-brometyl-cyanamid og 14,6 g- butylamin l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 137 - 138°; 38.8 g N-[p-(2-propionamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g-butylamine l-[p-(2-propionamido-ethyl)-phenylsulfonyl ]-2-imino-3-butyl-imidazolidine, m.p. 137 - 138°;

41,6 g N-[p-[2-(2-metyl-butyramido)-etyl]-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g butylamin I-[p-[2-(2-metyl-butyr- 41.6 g of N-[p-[2-(2-methyl-butyramido)-ethyl]-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of butylamine I-[p-[2-(2- methyl-butyr-

amido)-etyl]-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 114 - 116°; amido)-ethyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine, m.p. 114 - 116°;

41,6 g N-[p-(2-valeramido-etyl)-fenylsulfonyl]-N-2-bKometyl-cyanamid og 14,6 g butylamin l-[p-(2-valeramido-etyl)-fenylsul-fonyl]-2 -imino-3-butyl-imidazolidinet, smp. 130 } 41.6 g of N-[p-(2-valeramido-ethyl)-phenylsulfonyl]-N-2-bComethyl-cyanamide and 14.6 g of butylamine l-[p-(2-valeramido-ethyl)-phenylsulfonyl] -2-imino-3-butyl-imidazolidine, m.p. 130 }

41,6 g N-[p-(2-valeramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g isobutyl-amin l-[p-(2-valeramido-etyl)-fenylsu1 fonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 130°; 41.6 g N-[p-(2-valeramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g isobutylamine 1-[p-(2-valeramido-ethyl)-phenylsulfonyl ]-2-imino-3-isobutyl-imidazolidine, m.p. 130°;

50,0 g N-[p-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g isobutylamin l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-isobutyl-■imidazolidinet, smp. 117 - 119°; 50.0 g N-[p-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g isobutylamine l-[p-[2-(2 -methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-isobutyl-■imidazolidine, m.p. 117 - 119°;

42,8 g N-[p-(2-cykloheksan-karboksamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g isobutylamin l-[p-(2-cykloheksan-karboksamido-etyl)-venylsulfonyl]-2-imino-3-isobutyl-imidazolidinet, smp. 175 - 177°; 42.8 g of N-[p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of isobutylamine 1-[p-(2-cyclohexane-carboxamido-ethyl)- venylsulfonyl]-2-imino-3-isobutyl-imidazolidine, m.p. 175 - 177°;

37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g sek.butylamin l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. 106 - 108°; 37.4 g of N-[p-(2-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of sec.butylamine l-[p-(2-acetamido-ethyl)-phenylsulfonyl] -2-imino-3-sec.butyl-imidazolidine, m.p. 106 - 108°;

38,8 g N-[p-(2-propionamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g sek.butylamin l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-sek.butyl-imidazolidinet, smp. •40,2 g N-[p-(2-butyramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g sek.butylamin l-[p-(2-butyramido-etyl)-f enylsu1fonyl]-2-imino-3-s ek.butyl-imidazolidinet, smp. 38.8 g of N-[p-(2-propionamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of sec.butylamine l-[p-(2-propionamido-ethyl)-phenylsulfonyl] -2-imino-3-sec.butyl-imidazolidine, m.p. • 40.2 g of N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of sec.butylamine l-[p-(2-butyramido-ethyl)-f enylsulfonyl]-2-imino-3-s ec.butyl-imidazolidine, m.p.

40,2 g N-[p-(2-butyramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g tert.butylamin.l-[p-(2-butyramido-etyl)- 40.2 g of N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of tert.butylamine.1-[p-(2-butyramido-ethyl)-

fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. 148 - 149°; phenylsulfonyl]-2-imino-3-tert.butyl-imidazolidine, m.p. 148 - 149°;

41,6 g N-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 14,6 g tert.butylamin l-[p-(2-isovaleramido-etyl)-fenylsulfonyl]-2-imino-3-tert.butyl-imidazolidinet, smp. Ib2 - 154Q<->, 41.6 g of N-[p-(2-isovaleramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 14.6 g of tert-butylamine 1-[p-(2-isovaleramido-ethyl)-phenylsulfonyl] -2-imino-3-tert.butyl-imidazolidine, m.p. Ib2 - 154Q<->,

41,6 g N-[p-(2-valeramido-etyl)-fenylsulfonyl]-N-2-bromety1-cyanamid og 17 g cyklopentylamin l-[p-(2-va 1eramido-etyl)-f enylsulf onyl]-2-imino-3-cyk lopentyl-imidazo 1 idinet., .smp. 132 - 134°; 41.6 g of N-[p-(2-valeramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 17 g of cyclopentylamine 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]- 2-imino-3-cyclopentyl-imidazo 1 idinet., m.p. 132 - 134°;

40,2 g N-[p-(2-bu tyramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 17 g cyklopentylamin l-[p-t2-butyramido-etyl)-f enylsulfonyl]-2-imino-3-cyklopen tyl-imidazo1 id inet, smp. 40.2 g of N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 17 g of cyclopentylamine 1-[p-t2-butyramido-ethyl)-phenylsulfonyl]-2- imino-3-cyclopen tyl-imidazo1 id inet, m.p.

44,2 g N-[p-(2-cyklohek san-kårboksamido-etyl)- fenylsulfonyl]-N-2-brometyl-cyanamid' og 17 g cyklopentylamin l-[ p-( 2-cyk lohek s an-ka rboksamido-etyl)-fenylsu1 fonyl}-2-imino-3-cyklopentyl-imidazolidinet, smp. 178 - 179°. 44.2 g of N-[p-(2-cyclohexancarboxamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide' and 17 g of cyclopentylamine 1-[p-(2-cyclohexancarboxamido -ethyl)-phenylsulfonyl}-2-imino-3-cyclopentyl-imidazolidine, m.p. 178 - 179°.

b) U tgangsrnaterialet oppnås som folger: b) The starting material is obtained as follows:

Til .10,6 g brorncyan i 40 ml eter tildryppes v ed -KT 4,3 g To .10.6 g of brorn cyan in 40 ml of ether, add -KT 4.3 g

etylenimin i 20 ml eter. Det dannede i eter uopplbselige 2-brometyl-cyanamid tilsettes nå- en suspensjon av 27,6 g p-(2-propionamido-etyl)-fenylsulfoklorid i 100 ml aceton. Derpå tildrypper man b2 ml 2-n natronlut og rorer i 1 time ved værelsetemperatur. Nå fjernes eter og aceton i rotasjonsfordamperen. Substansen ekstraheres med metylenklorid. Opplosningen vaskes to ganger med" 20 ml vann, torkes og inndampes. Resten,. N.-[ p-(- 2-pro pi on am ido -et yl) - f-enylsul fon yl] - N.-2-brometyl-cyanamidet, er en svak gul olje. ethyleneimine in 20 ml of ether. The ether-insoluble 2-bromomethylcyanamide formed is now added to a suspension of 27.6 g of p-(2-propionamido-ethyl)-phenylsulfochloride in 100 ml of acetone. Then b2 ml of 2-n caustic soda is added drop by drop and stirred for 1 hour at room temperature. Ether and acetone are now removed in the rotary evaporator. The substance is extracted with methylene chloride. The solution is washed twice with 20 ml of water, dried and evaporated. The residue,. -the cyanamide, is a faint yellow oil.

De anvendte ikke isolerte utgangsprodukter oppnås på analog måte fra 10,6- g brorncyan og 4,3 g etylenimin og: 26,2 g p-(2-acetamido-etyl)-fenylsulfoklorid N-[p-(2-acetamido-etyl )-fenylsulfon yl] -N-2-brometylcyanamide t; The non-isolated starting products used are obtained in an analogous manner from 10.6 g bronn cyan and 4.3 g ethyleneimine and: 26.2 g p-(2-acetamido-ethyl)-phenylsulfochloride N-[p-(2-acetamido-ethyl) )-phenylsulfonyl]-N-2-bromomethylcyanamide t;

29,0 g p-(2-butyramido-etyl)-fenylsulfoklorid N-[p-(2-butyramido-etyl) -f en ylsulfonyl] -N-2-brometylcyanamidet; 29.0 g of p-(2-butyramido-ethyl)-phenylsulfochloride N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethylcyanamide;

30,4 g p-[2-(2-metyl-butyramido)-etyl]-fenylsulfoklorid N-[p-[2-(2-metyl-butyramido)-etyl]- fenylsulfonyl]-N-2-brometyl-cyanamidet; 30.4 g p-[2-(2-methyl-butyramido)-ethyl]-phenylsulfochloride N-[p-[2-(2-methyl-butyramido)-ethyl]-phenylsulfonyl]-N-2-bromomethyl-cyanamide ;

,30,4 g p-(-2-valeramido-etyl)-f enylsulf ok lorid N-[ p-( 2-valeramido-etyl)-fenylsulfonyl]-N-2-brome tylcyanamidet; , 30.4 g p-(-2-valeramido-ethyl)-phenylsulfonyl chloride N-[ p-(2-valeramido-ethyl)-phenylsulfonyl]-N-2-bromoethylcyanamide;

30,4 g p-(2-isovaleramido-etyl)-fenylsulfoklorid N-[p-(2-iso-valeramido-etyl)-fenylsu Tf onyl]-N-2-brometylcyanamidet; 30.4 g of the p-(2-isovaleramido-ethyl)-phenylsulfochloride N-[p-(2-iso-valeramido-ethyl)-phenylsulfonyl]-N-2-bromomethylcyanamide;

3b,5 g p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfoklorid N-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfonyl]-N-2-brometyl-cyanamidet ; 3b.5 g p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfochloride N-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-N-2-bromomethyl-cyanamide ;

39,0 g p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfoklorid N-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-N-2-brometyl cyanamidet. 39.0 g p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfochloride N-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl] -N-2-bromomethyl cyanamide.

EKSEMPEL 43 EXAMPLE 43

a) 38,8 g N-[p-(2-propionamido-etyl)-fenylsulfonyl]-N-2-brom-etylcyanamid oppvarmes i 200 ml alkohol med 19,8 g cykloheksylamin i 1 time under tilbakelop. Derpå inndampes reaksjonsblandingen i rotasjonsfordamperen. Resten fortynnes med 50 ml a) 38.8 g of N-[p-(2-propionamido-ethyl)-phenylsulfonyl]-N-2-bromo-ethylcyanamide are heated in 200 ml of alcohol with 19.8 g of cyclohexylamine for 1 hour under reflux. The reaction mixture is then evaporated in the rotary evaporator. The residue is diluted with 50 ml

eddikester og ekstraheres to ganger med 80 ml 2-n saltsyre. Den vandige fase innstilles alkalisk med 2-n natronlut og utrystes to ganger med 100 ml metylenklorid.. Metylenkloridopplbsningen vaskes med vann, tbrkes og inndampes. Resten krystalliseres fra eddikester og gir det rene l-[p-(2-propionamido-etyl) -f enylsu 1 fon yl] -2- imino-3-cyk loh ek syl -imidazol idin-h em i-hydrat med smp. 110 - 112°. acetic acid and extracted twice with 80 ml of 2-N hydrochloric acid. The aqueous phase is made alkaline with 2-n sodium hydroxide solution and shaken twice with 100 ml of methylene chloride. The methylene chloride solution is washed with water, dried and evaporated. The residue is crystallized from acetic ester and gives the pure 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidin-hemi-hydrate with m.p. 110 - 112°.

På analog måte oppnår man fra: Analogously, one obtains from:

36,0 g N-[p-(2-formamido-etyl)-fenylsulfonyl-N-2-brometyl- 36.0 g N-[p-(2-formamido-ethyl)-phenylsulfonyl-N-2-bromomethyl-

cyanamid og 19,8 g cykloheksylamin l-[p-(2-formamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 135 - 136°; cyanamide and 19.8 g of the cyclohexylamine 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine, m.p. 135 - 136°;

37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl- 37.4 g of N-[p-(2-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-

cyanamid og 19,8 g cykloheksylamin l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazo1 id in et, smp. 181 - 183°; cyanamide and 19.8 g of cyclohexylamine 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazo1ide in et, m.p. 181 - 183°;

40,2 g N-[p-(2-N-mety1-acetamido-propyl)-fenylsulfonyl]-N-2-brornetylcyanamid og 19,8 g cykloheksylamin l-[ p-( 2-N-mety 1 - a c et amido-propyl) - f enyl sul fonyl]' -2- imino-3- cyk loheks yl - imidazolidinet, smp. 108 - 110°; 40.2 g of N-[p-(2-N-methyl-acetamido-propyl)-phenylsulfonyl]-N-2-bromomethylcyanamide and 19.8 g of cyclohexylamine l-[p-(2-N-methyl-acetate) amido-propyl)-phenylsulfonyl]'-2-imino-3-cyclohexyl-imidazolidine, m.p. 108 - 110°;

40,2 g N-[p-(2-butyramido-etyl)-fenylsulfonyl]-N-2-brometyl-.cyanamid og 1.9,8 g cykloheksylamin l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-im.idazolidin • 1 H^O, 40.2 g N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-.cyanamide and 1.9.8 g cyclohexylamine 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]- 2-imino-3-cyclohexyl-im.idazolidine • 1 H^O,

smp. 143 - 144°; m.p. 143 - 144°;

41 ,6 g N-[ p-( 2-valeramido-e tyl)-f enylsulf onyl ]-N-2-brorne tyl-cyanamid og cykloheksylamin l-[p-(2-valeramido-etyl)-fenyl-su lfonyi]-2 -imino-3-cykloheksyl-imidazolidin ■ 1/4 HjO, srnp. 154 - 155°; 41,6 g N-[p-(2-Isovaleramido-etyl)-fenylsu1 fonyl]-N-2-brometyl-cyanamid og cykloheksylamin 1-[p-(2-1sovaleramido-etyl)-fenyl-sulfonyl]-2-imino-3-cykloheksyl-imidazolidinet, smp. 180 - 181°; 46,6 g N-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfonylJ-N-2-brometylcyan.amid og cykloheksylamin I-[ p-[ 2-( 3-metoksy-benzamido }- etyl ] - f enylsul f onyl ] - 2-imiiro-3-cyklohek syl-imida zoLidinet, smp. 167 - 168°; 42,8- g N-[p-(2-cykloheksan-karboksamido-etyl)-fenylsulfonyl]-N-2-brometyl-cy.anamid og cykloheksylamin. l-[ p-( 2-cyk loheksan-k årbok sam ido-et yl) - f enyl sulf onyl ]'-2- imino-3- cyklohek syl - imidazolidinet,- smp-. 167 - 168°; 37,4 g N-[p-(2-acetamido-etyl)-fenyisulfonyl]-N-2-brometylcyan-amid og cykloheptylamin l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheptyl-imidazolidinet, smp. 166 - 167°; 40,2 g N-[p-(2-butyramido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og cykloheptylamin l-[p-(2-butyramido-etyl)-fenylsul-fonyl]-2 -imino-3-cykloheptyl-imidazolidinet, smp. 37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 20,2 g heksylamin l-[p-(2-acetamido-etyl)-fenyl-su lfonyl]-2-imino-3-heksyl-imidazolidinet, smp. 136 - 137°; 37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 22,8 g tert.oktylamin l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-tert.oktyl-imidazo1idinet, smp. 131 - 135°; 37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 11,4 g allylamin 1-[p-(2-acetamido-etyl)-fenylsul fonyl]-2-imino-3-allyl-imidazolidinet, smp. 127 - 129<0>', 40,2 g N-[p-(2-butyramido-etyl)-fenylsul fonyl]-N-2-brometyl-cyanamid og 11,4 g allylamin l-[p-(2-butyramido-etyl)-fenyl-sulfonyl] -2-imino-3-allyl-imidazolidinet, smp. 122 - 124°; 37,4 g N-[p-(2-acetamido-etyl)-fenylsulfonyl]-N-2-brometyl-cyanamid og 24,2 g fenetylamin l-[p-(2-acetamido-etyl)-fenylsu1-fonyl]-2-imino-3-fenetyl-imidazolidinet, smp. 148 - 150°. b) De anvendte ikke isolerte utgangsprodukter oppnås analogt eksempel 42b) fra 10,6 g brorncyan og 4,3 g etylenimin og: 24,8 g p-(2-formamido-etyl)-fenylsulfoklorid N-[p-(2-formamido-etyl )-fenylsulfonyl]-N-2-brometylcyanamidet; 41.6 g of N-[p-(2-valeramido-ethyl)-phenylsulfonyl]-N-2-brorne ethyl-cyanamide and cyclohexylamine l-[p-(2-valeramido-ethyl)-phenyl-sulfonyl ]-2 -imino-3-cyclohexyl-imidazolidine ■ 1/4 HjO, srnp. 154 - 155°; 41.6 g N-[p-(2-Isovaleramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and cyclohexylamine 1-[p-(2-1sovaleramido-ethyl)-phenyl-sulfonyl]-2- the imino-3-cyclohexyl-imidazolidine, m.p. 180 - 181°; 46.6 g of N-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl I-N-2-bromomethylcyanamide and cyclohexylamine I-[ p-[ 2-(3-methoxy-benzamido }- ethyl]-phenylsulfonyl]-2-imiro-3-cyclohexyl-imidazoLidine, mp 167 - 168°; 42.8 g N-[p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfonyl] -N-2-bromomethyl-cyanamide and cyclohexylamine.1-[p-(2-cyclohexane-cyclohexyl)-phenylsulfonyl]'-2-imino-3-cyclohexyl-imidazolidine ,- m.p. 167 - 168°; 37.4 g N-[p-(2-acetamido-ethyl)-phenysulfonyl]-N-2-bromomethylcyanamide and cycloheptylamine 1-[p-(2-acetamido-ethyl) )-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, mp 166 - 167°, 40.2 g of N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and cycloheptylamine 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazolidine, m.p. 37.4 g N-[p-(2-acetamido-ethyl)-phenylsulfonyl] -N-2-bromomethyl-cyanamide and 20.2 g of hexylamine 1-[p-(2-acetamido-ethyl)-phenyl-sulfonyl]-2-imino-3-hexyl-imidazolidine, mp 136-137°; 37.4 g N- [p-(2-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 22.8 g of tert.octylamine 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3 -tert.octyl-imidazo1idine, m.p. 131 - 135°; 37.4 g of N-[p-(2-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 11.4 g of allylamine 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]- The 2-imino-3-allyl-imidazolidine, m.p. 127 - 129<0>', 40.2 g of N-[p-(2-butyramido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 11.4 g of allylamine 1-[p-(2- butyramido-ethyl)-phenyl-sulfonyl]-2-imino-3-allyl-imidazolidine, m.p. 122 - 124°; 37.4 g N-[p-(2-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethyl-cyanamide and 24.2 g phenethylamine 1-[p-(2-acetamido-ethyl)-phenylsulfonyl] -2-imino-3-phenethyl-imidazolidine, m.p. 148 - 150°. b) The non-isolated starting products used are obtained analogously to example 42b) from 10.6 g bronn cyan and 4.3 g ethyleneimine and: 24.8 g p-(2-formamido-ethyl)-phenylsulfochloride N-[p-(2-formamido) -ethyl)-phenylsulfonyl]-N-2-bromomethylcyanamide;

27,6 g p-(2-N-metyl-acetamido-etyl)-fenylsulfoklorid N-[p-(2-N-metyl-acetamido-etyl)-fenylsulfonyl]-N-2-brometylcyanamidet; 27.6 g of the p-(2-N-methyl-acetamido-ethyl)-phenylsulfochloride N-[p-(2-N-methyl-acetamido-ethyl)-phenylsulfonyl]-N-2-bromomethylcyanamide;

32,6 g p-[2-cykloheksan-karboksamido-etyl)-fenylsulfoklorid N-[p-(2-cykloheksan-karboksamido-etyl)-fenylsulfonyl]-N-2-brom-etylcyanamidet. 32.6 g of p-[2-cyclohexane-carboxamido-ethyl)-phenylsulfochloride N-[p-(2-cyclohexane-carboxamido-ethyl)-phenylsulfonyl]-N-2-bromo-ethylcyanamide.

EKSEMPEL 44 EXAMPLE 44

42,4 g l-[p-(2-arninoetyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid tilsettes 110 ml 2-n natronlut, og den frisatte base ekstraheres med metylenklorid. Til den torkede opplosning tilsettes 14,7 g kloral. Etter 30 minutter avdestilleres opplbsningsmidlet. Resten oppvarmes under vann-strålevakuum i 10 minutter til ca. 65° og opplbses derpå i varm eddikester. Etter avkjoling krystalliserer l-[p-(2-formamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidinet. 42.4 g of 1-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine dihydrochloride are added to 110 ml of 2-n caustic soda, and the released base is extracted with methylene chloride. 14.7 g of chloral is added to the dried solution. After 30 minutes, the solvent is distilled off. The residue is heated under a water jet vacuum for 10 minutes to approx. 65° and then dissolved in hot vinegar. After cooling, the 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclohexyl-imidazolidine crystallizes.

Det smelter ved 13b - 136°. It melts at 13b - 136°.

På analog måte oppnår man fra 14,7 g kloral og: In an analogous way, one obtains from 14.7 g of chloral and:

31,O g l-[ p-(2-aminoetyl)-fenylsulfonyl]-2-imino-3-propyl-imidazolidin l-[p-(2-formamido-etyl)-fenylsulfonyl]- 2-im ino-3-propyl-imidazolidinet, smp. 103 - 104°", 31,0 g l-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-propyl-imidazolidine l-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3- propyl-imidazolidine, m.p. 103 - 104°",

31,0 g l-[p-(2 -arninoe tyl)-fenylsulfonyl]-2- imino-3-i sopropyl-imidazolidin l-[ p- (2-formam ido-e tyl)-fenylsulfonyl]-2-imino-3-isopropyl-imidazo1idinet, smp. 112 - 113°; 31.0 g 1-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-isopropyl-imidazolidine 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino -3-isopropyl-imidazo1idine, m.p. 112 - 113°;

32,4 g l-[p-(2-aminoetyl)-fenylsulfonyl]-2-irnino-3-butyl-imidazolidin l-[p-(2-formamido-etyl)-fenylsulfonyl]-2-imino-3-butyl-imidazolidinet, smp. 111 - 112°; 32.4 g 1-[p-(2-aminoethyl)-phenylsulfonyl]-2-irnino-3-butyl-imidazolidine 1-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3-butyl -imidazolidine, m.p. 111 - 112°;

32,4 g 1-[p-(2-aminoetyl)- f enyl sul fonyl]-2-imino-3-isobutyl-imidazolidin l-[p- (.2- f ormam i do - etyl) - f enylsul f onyl ].-2- Imino-3-isobutyl-imidazolidinet, smp. 107 - 108°; 32.4 g 1-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-isobutyl-imidazolidine 1-[p-(.2-formamido-ethyl)-phenylsulf onyl ].-2- Imino-3-isobutyl-imidazolidine, m.p. 107 - 108°;

36-,4 g l-[p-(2-aminoetyl)-fenylsulfonyl]-2- imino—3-cyk loheptyl - imidazol Idin l-[p- t2-formami do-et yl).-f en ylsulfonyl ]-2- imino-3-cykloheptyl-imidazolidinet,- smp. 130. - 133°; 36-.4 g l-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-cycloheptyl-imidazole Idyne l-[p-t2-formamido-ethyl).-phenylsulfonyl]- 2-imino-3-cycloheptyl-imidazolidine, - m.p. 130. - 133°;

36,4 g- 1-[p-(2-aminoetyl)-fenylsulfonyl]-2-imino-3-(2-metyl- 36.4 g- 1-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-(2-methyl-

cyk loheksyl)- imidazol idin l-[ p- ( 2- f orm am Ido- etyl )-fenylsulfonyl]-2-imino-3-(2-metyl-cykloheksyl)-imidazolidinet, smp. 127 - 129°; cyclohexyl)-imidazolidine 1-[p-(2- form amido-ethyl)-phenylsulfonyl]-2-imino-3-(2-methyl-cyclohexyl)-imidazolidine, m.p. 127 - 129°;

36,4 g l-[p-(2-aminoetyl)-fenylsulfonyl]-2-imino-3-(4-metyl-cyk loh ek syl)- imidazol Idin l-[ p-( 2-formamido-etyl)- f enylsul fonyl]-2-imino-3-(4-metyl-cykloheksyl)-imidazolidinet, smp. 126 - 128°<;>36.4 g l-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexyl)-imidazole Idyne l-[p-(2-formamido-ethyl)- phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexyl)-imidazolidine, m.p. 126 - 128°<;>

33,6 g l-[p-(2-aminoetyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin l-[p-(2-formamido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidinet, smp. 108 - 110°; 33.6 g l-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl-imidazolidine l-[p-(2-formamido-ethyl)-phenylsulfonyl]-2-imino-3-cyclopentyl -imidazolidine, m.p. 108 - 110°;

42,1 g l-[p-(2-aminoetyl)-fenylsulfonyl]-2-imino-3-(3-cyklo-h ek s en-1-yl)- imidazol idin l-[ p-( 2- formamido- etyl) - f enylsu lfonyl]-2-imino-3-(3-cykloheksen-l-yl)-imidazolidinet, smp. 116 - 118°. 42.1 g l-[p-(2-aminoethyl)-phenylsulfonyl]-2-imino-3-(3-cyclo-hexen-1-yl)-imidazolidine l-[p-(2-formamido -ethyl)-phenylsulfonyl]-2-imino-3-(3-cyclohexen-1-yl)-imidazolidine, m.p. 116 - 118°.

EKSEMPEL 45 EXAMPLE 45

a) På analog måte som i eksemplene 15 a - 33a oppnår man ved acylering: ' l-[p-[2-(2-metoksy-5-klor-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-metyl-imidazolidin, smp. 140 - 141°; 1 - [ p- ( 2-acetamido-propyl) - fenylsulfonyl]-2-irnino-3-butyl-imidazolidin, smp. 120 - 122°; 1-[p-[2-(N-metyl-acetamido)-propyl]-f enylsulfonyl]-2-imino-3-butyl-imidazolidin ' F^O, smp. 80 - 82°; l-[p-[l-(2-klorbenzamido)-etyl]-fenylsulfonyl]-2-imino-3-tert. butyl-imidazolidin, smp. 166 - 168°; l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-allyl-imidazolidin, smp. 122 - 124°-, l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-heksyl-imidazolidin, smp. 136 - 137°; l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-heksyl-imidazolidin, smp. 124 - 126°; l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-(2-metyl-cykloheksan-l-yl)-imidazolidin, smp. 134 - 136°; l-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-(2-metyl-cykloheksan-l-yl)-imidazolidin, smp. 17b - 176°; l-[p-[2-(3,4-dimetoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-(2-metyl-cykloheksan-l-yl)-imidazolidin, smp. 184 - 186°; l-[p-(2-acetamido-etyl)-fenylsulfonyl]-2-imino-3-(3-cyklohek sen-1-yl)-imidazolidin, smp. 171 - 173°; 1-[p-( 2-bu tyr am ido-etyl)- f enylsu lf on yl]-2-irn i no-3-( 3-cyk loheks en-1-yl)-imidazol idin , smp. 127 - 129°; l-[p-(2-acetamido-etyl)-fenylsulfonylj-2-imino-3-fenetyl-imidazolidin, srnp. 148 - lbO°<; >l-[p-(2-butyramido-etyl)-fenylsulfonyl]-2-imino-3-fen etyl-imida zol idin , smp. 136 - 138°;. l-[p-(2-valeramido-etyl)-fenylsulfonyl]-2-imino-3-fenetyl-imidazolidin, srnp. 122 - 123°; l-[ p - ( 2-ac etamido-etyl)-fenylsulfonyl]-2-imino-3-(l-metyl-2-f enetyl)-imidazolidin , smp.- 118 - 121°; l-[ p - ( 2 - bu tyramido-et yl)'- f enyl sulfonyl] - 2- imino-3 - (l-metyl-2-fenetyl)-imidazolidin, smp. 126 - 128°; l-[p-(2-ac etamido-etyl)- f enylsulfonyl]-2-imino-3-propyl-5-me-tyl-imidazolidin, smp. 121 - 122°; l-[p-(2-propionamido-etyl)-fenylsulfonyl]-2-imino-3-propyl-5-metyl-imidazolldln, smp-. 149 151°; l-[p-(2-butyramido-etyl)-f enylsulfonyl]-2-imino-3-propyl-5-metyl-imidazolidin, smp. 132 - 133°; l-[p-[2-(3-cykloheksyl -propionamido)- etyl]- f enylsulfonyl]-2-imino-3-propyl-5-metyl-imidazolidin, smp. 110 - 111°; l-[p-(2-ak ryiamido-etyl)- f enylsulfonyl]-2-imino-3-propyl-5-metyl-imidazolidin, smp. 128 - 129°; l-[p-[2-(3-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-(3-cykloheksen-l-yl)-imidazolidin, smp. 153 - 154°; 1-[p-(2-bu t<y>ramido-et<y>l)-f en<y>lsulfonyl]-2-imino-3-(4-metyl-cykloheksan-l-yl)-imidazolidin, smp. 135 - 136°; 1-Cp~[2-( 1-met yl-3 - cyk loheks en-k årboks amido )-etyl]-fenylsulfo-'_ nyl]-2-imino-3-(4-metyl-cykloheksan-1- yl)-imidazolidin, smp. 137 - 138,5°-, i-[P"[2-(3-metoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-(4-metyl-cykloheksan-l-yl)-imidazolidin, smp. 155 - 158°; l-[p-[2-(3,4-dimetoksy-benzamido)-etyl]-fenylsulfonyl]-2-imino-3-(4-metyl-cykloheksan-l-yl)-imidazolidin, smp. 193 - 195°; l-[p-(2-akrylamido-etyl)-fenylsulfonyl]-2-imino-3-(3-cyklohek-sen-l-yl)-imidazolidin, smp. 160 - 161°. b) De for omsetningen nodvendige aminoforbindelser som utgangsprodukter er beskrevet i eksemplére 15b - 33b eller oppnås analogt eksemplene 15b - 33b: l-[ p - ( 2-amino-etyl.) - f enylsulf onyl] - 2-imino-3 - ( 3-cyk loheks en-1-yl)-imidazolidin, smp. 245 - 247°; l-[p-(2-amino-etyl)-f enylsulfonyl]-2-imino-3-(4-metyl-cykloheksan-l-yl)-imidazolidin , smp. 260°; 1 - [ p- (2-amino-etyl) -fenylsulfonyl]-2-imino-3-(2-metyl-cykloheksan-l-yl)-imidazolidin, glassaktig smelte; l-[p-(2-amino-etyl)- fenylsulfonyl]-2-imino-3-heksyl-imidazolidin, smp. 219 - 222°; l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-fenetyl-imidazolidin, smp. 229 - 236°; l-[p-(2-amino-etyl)-f enyl sulfonyl]-2-imino-3-(l-metyl-2-fenetyl)-imidazolidin , glassaktig smelte; l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-alkyl-imidazolidin, smp. 232 - 234°. a) In an analogous manner as in examples 15 a - 33 a, one obtains by acylation: '1-[p-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3- methyl-imidazolidine, m.p. 140 - 141°; 1 - [p-(2-acetamido-propyl)-phenylsulfonyl]-2-irnino-3-butyl-imidazolidine, m.p. 120 - 122°; 1-[p-[2-(N-methyl-acetamido)-propyl]-phenylsulfonyl]-2-imino-3-butyl-imidazolidine ' F 2 O, m.p. 80 - 82°; 1-[p-[1-(2-chlorobenzamido)-ethyl]-phenylsulfonyl]-2-imino-3-tert. butyl-imidazolidine, m.p. 166 - 168°; 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-allyl-imidazolidine, m.p. 122 - 124°-, 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-hexyl-imidazolidine, m.p. 136 - 137°; 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-hexyl-imidazolidine, m.p. 124 - 126°; 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-(2-methyl-cyclohexan-1-yl)-imidazolidine, m.p. 134 - 136°; 1-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-(2-methyl-cyclohexan-1-yl)-imidazolidine, m.p. 17b - 176°; 1-[p-[2-(3,4-dimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-(2-methyl-cyclohexan-1-yl)-imidazolidine, m.p. 184 - 186°; 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-(3-cyclohexen-1-yl)-imidazolidine, m.p. 171 - 173°; 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-irinino-3-(3-cyclohexen-1-yl)-imidazolidine, m.p. 127 - 129°; 1-[p-(2-acetamido-ethyl)-phenylsulfonyl l-2-imino-3-phenethyl-imidazolidine, srnp. 148 - lbO°<; >1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-phen ethyl-imidazolidin, m.p. 136 - 138°; 1-[p-(2-valeramido-ethyl)-phenylsulfonyl]-2-imino-3-phenethyl-imidazolidine, srnp. 122 - 123°; 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-(1-methyl-2-phenethyl)-imidazolidine, mp 118-121°; 1-[p-(2-butyramido-ethyl)'-phenylsulfonyl]-2-imino-3-(1-methyl-2-phenethyl)-imidazolidine, m.p. 126 - 128°; 1-[p-(2-acetamido-ethyl)-phenylsulfonyl]-2-imino-3-propyl-5-methyl-imidazolidine, m.p. 121 - 122°; 1-[p-(2-propionamido-ethyl)-phenylsulfonyl]-2-imino-3-propyl-5-methyl-imidazolidln, m.p. 149 151°; 1-[p-(2-butyramido-ethyl)-phenylsulfonyl]-2-imino-3-propyl-5-methyl-imidazolidine, m.p. 132 - 133°; 1-[p-[2-(3-cyclohexyl-propionamido)-ethyl]-phenylsulfonyl]-2-imino-3-propyl-5-methyl-imidazolidine, m.p. 110 - 111°; 1-[p-(2-acylamido-ethyl)-phenylsulfonyl]-2-imino-3-propyl-5-methyl-imidazolidine, m.p. 128 - 129°; 1-[p-[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-(3-cyclohexen-1-yl)-imidazolidine, m.p. 153 - 154°; 1-[p-(2-bu t<y>ramido-eth<y>l)-phen<y>lsulfonyl]-2-imino-3-(4-methyl-cyclohexan-1-yl)-imidazolidine, m.p. 135 - 136°; 1-Cp~[2-(1-methyl-3-cyclohexene-boxamido)-ethyl]-phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexan-1-yl )-imidazolidine, m.p. 137 - 138.5°-, i-[P"[2-(3-methoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexan-1-yl)-imidazolidine, mp 155 - 158°; 1-[p-[2-(3,4-dimethoxy-benzamido)-ethyl]-phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexan-1-yl)-imidazolidine , mp 193 - 195°; 1-[p-(2-acrylamido-ethyl)-phenylsulfonyl]-2-imino-3-(3-cyclohexen-1-yl)-imidazolidine, mp 160 - 161° b) The amino compounds required for the reaction as starting products are described in examples 15b - 33b or are obtained analogously to examples 15b - 33b: l-[p - (2-amino-ethyl.) - phenylsulfonyl] - 2-imino-3 - (3-cyclohexen-1-yl)-imidazolidine, mp 245 - 247°; 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-(4-methyl-cyclohexane -1-yl)-imidazolidine, mp 260°; 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-(2-methyl-cyclohexan-1-yl)-imidazolidine, glassy melt; 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-hexyl-imidazolidine, mp 219 - 222°; 1-[p-(2-amino-ethyl)-phenylsulfonyl] -2-imino-3-phenethyl-imidazolidine, mp 229 - 236°; 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-(1-methyl-2-phenethyl)-imidazolidine, glassy melt; 1-[p-(2-amino-ethyl)-phenylsulfonyl]-2-imino-3-alkyl-imidazolidine, m.p. 232 - 234°.

Claims (1)

Analogifremgangsmåte for fremstilling av farmakologisk aktive, i nye derivater av I-(p-aminoalkyl-fenylsulfonyl)-2-imino-imidazolidin med den generelle formel I,Analogous process for the preparation of pharmacologically active, in new derivatives of I-(p-aminoalkyl-phenylsulfonyl)-2-imino-imidazolidine of the general formula I, hvor rn er 2 eller 3, . R-^ betyr en alkylgruppe med hoyst 12 karbonatomer, en alkenylgruppe med 3-5 karbonatomer, en cykloalkyl-eller cykloalkenylgruppe med hoyst 7 karbonatomer eller en fenylalkylgruppe med hoyst 9 karbonatomer, R2 hydrogen eller en .alkylgruppe med hoyst 2 karbon- atomer, R~ hydrogen, en alkylgruppe eller kloralkylgruppe med hoyst 7 karbonatomer, en alkenylgruppe med hoyst 5 kar bonatomer, en cykloalkyl- eller cykloalkenylgruppe med hoyst 8 karbonatomer, en fenylgruppe eller en fenylalkyl-eller fenylalkenylgruppe med hoyst 10 karbonatomer, idet den som R^ henh. i R^ foreliggende fenylgruppe kan være .substituertjmed halogen inntil atomnummer 35, trifluormetylgrupper, alkylgrupper med hoyst 4 karbonatomer, hydroksylgrupper, alkoksy- eller alkyltiogrupper med hoyst 2 karbonatomer,enkelt til tredobbelt, og R^ hydrogen eller metylgruppen, og deres addisjonssalter med uorganiske eller organiske syrer, karakterisert ved at a) man omsetter et reakspnsdyktig funksjonelt derivat av en sulfonsyre med den generelle formel II, hvor m, R^ og R^ har den under formel I angitte betydning, ,. med en forbindelse .med den generelle formel III, <*>' hvor R^ og R2 har d en under formel I angitte betydning, og overforer eventuelt reaksjonsproduktet med en uorganisk eller organisk syre til et addisjonssalt, eller b) man omsetter en syre med den generelle formel IV, hvor R- har den under formel I angitte betydning, eller et reaksjonsdyktig funksjonelt derivat av en slik syre med en forbindelse med den generelle formel V, hvor m, Rp R2 og R. har den under formel I angitte be tydn ing, og overforer eventuelt reaksjonsproduktet med en uorganisk eller organisk syre til et addisjonssa.lt, eller c) man kondenserer forbindelser med den generelle formel VII, hvor m, R^, R2> R3 °9 ^4 nar den under formel I angitte betydning og R^ betyr hydrogen, en arylmetyl-, diarylmetyl- eller en triarylmetylgruppe, metyl- eller allylgruppen, med et reaksjonsdyktig cyansyrederivat under ringslutning eventuelt under avspaltning av et R^-halogenid og overforer eventuelt de erholdte forbindelser med en uorganisk eller organisk syre til et addisjonssalt, eller d) man kondenserer forbindelser med den generelle formel VIII, hvor m, R^ og R^ har den under formel I angitte betydning, med en reaksjonsdyktig ester åv en hydroksyforbindelse med den generelle formel IX, hvor og R2 har den under formel I angitte betydning, under ringslutning og overforer eventuelt den erholdte forbindelse med en uorganisk eller organisk syre til et addisjonssalt , eller e) man kondenserer en reaksjonsdyktig ester av en forbindelse med den generelle formel X, hvor m, R^ i R3 og R. har den under formel I angitte betydning, med et amin med den generelle formel XI, R1 - NFf, (XI) hvor R^ har den under formel* .1 angitte betydning, og cykliserer og overforer eventuelt den erholdte forbindelse med en uorganisk eller organisk syre til et addisjonssa 11, eller f) når nye derivater av 1-(p-aminoalkyl-fenylsulfonyl)-2-imino-imidazolidin med den generelle formel I, "hvor R_ dog bare kan bety hydrogen, skal fremstilles, formylerer man forbindel- ser med den generelle formel XII, hvor m, R-p R^ og R^ har den under formel I angitte betydning, med kloral og overforer eventuelt de erholdte forbindelser med en uorganisk eller organisk syre til et addisjonssalt.where rn is 2 or 3, . R-^ means an alkyl group with a maximum of 12 carbon atoms, an alkenyl group with 3-5 carbon atoms, a cycloalkyl or cycloalkenyl group with a maximum of 7 carbon atoms or a phenylalkyl group with a maximum of 9 carbon atoms, R2 hydrogen or an alkyl group with no more than 2 carbon atoms, R~ hydrogen, an alkyl group or chloroalkyl group with no more than 7 carbon atoms, an alkenyl group with no more than 5 carbon atoms bon atoms, a cycloalkyl or cycloalkenyl group with no more than 8 carbon atoms, a phenyl group or a phenylalkyl or phenylalkenyl group with no more than 10 carbon atoms, as R in R^ the phenyl group present can be substituted by halogen up to atomic number 35, trifluoromethyl groups, alkyl groups with at most 4 carbon atoms, hydroxyl groups, alkoxy or alkylthio groups with at most 2 carbon atoms, single to triple, and R^ hydrogen or the methyl group, and their addition salts with inorganic or organic acids, characterized in that a) a reactive functional derivative of a sulfonic acid of the general formula II, where m, R^ and R^ have the meaning given under formula I, ,. with a compound of the general formula III, <*>' where R^ and R2 have the meaning given under formula I, and possibly transfer the reaction product with an inorganic or organic acid to an addition salt, or b) one reacts an acid with the general formula IV, where R- has the meaning given under formula I meaning, or a reactive functional derivative of such an acid with a compound of the general formula V, where m, Rp R 2 and R. have the meaning given under formula I, and optionally transfer the reaction product with an inorganic or organic acid to an addition salt, or c) one condenses compounds with the general formula VII, where m, R^, R2 > R3 °9 ^4 when the meaning given under formula I and R ^ means hydrogen, an arylmethyl, diarylmethyl or a triarylmethyl group, the methyl or allyl group, with a reactive cyanic acid derivative during ring closure, possibly during cleavage of an R^-halide and optionally transferring the compounds obtained with an inorganic or organic acid to an addition salt, or d) one condenses compounds with the general formula VIII , where m, R^ and R^ have the meaning given under formula I, with a reactive ester of a hydroxy compound of the general formula IX, where and R2 has the meaning given under formula I, during ring closure and possibly transferring the obtained compound with an inorganic or organic acid to an addition salt, or e) one condenses a reactive ester of a compound of the general formula X, where m, R ^ in R3 and R. has the meaning given under formula I, with an amine of the general formula XI, R1 - NFf, (XI) where R^ has the meaning given under formula* .1, and optionally cyclizes and transfers the obtained compound with an inorganic or organic acid to an addition sa 11, or f) when new derivatives of 1-(p-aminoalkyl-phenylsulfonyl)-2-imino-imidazolidine with the general formula I, "where R_ however can only mean hydrogen, is to be produced, one formylates the connecting looks with the general formula XII, where m, R-p R^ and R^ have the under formula I indicated meaning, with chloral and optionally transfers the compounds obtained with an inorganic or organic acid to an addition salt.
NO69968A 1968-03-14 1969-03-07 NO124726B (en)

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