NO149027B - DEVICE FOR AA APPLYING A COAT ON A DOWN SURFACE - Google Patents
DEVICE FOR AA APPLYING A COAT ON A DOWN SURFACE Download PDFInfo
- Publication number
- NO149027B NO149027B NO764073A NO764073A NO149027B NO 149027 B NO149027 B NO 149027B NO 764073 A NO764073 A NO 764073A NO 764073 A NO764073 A NO 764073A NO 149027 B NO149027 B NO 149027B
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- NO
- Norway
- Prior art keywords
- pyrimidine
- sulfanilamide
- water
- methoxy
- compound
- Prior art date
Links
- -1 2-sulfanilamide-5-methoxy-pyrimidine Chemical compound 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- CGRKCGWEOIQFRD-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonylazanide Chemical class [Na+].NC1=CC=C(S([NH-])(=O)=O)C=C1 CGRKCGWEOIQFRD-UHFFFAOYSA-N 0.000 description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910019093 NaOCl Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AAYHVAIEYCLGGO-UHFFFAOYSA-N 2-ethylsulfanyl-5-methoxypyrimidine Chemical compound C(C)SC1=NC=C(C=N1)OC AAYHVAIEYCLGGO-UHFFFAOYSA-N 0.000 description 2
- VZZFSIFKVARSJZ-UHFFFAOYSA-N 5-methoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CN=C(S(C)(=O)=O)N=C1 VZZFSIFKVARSJZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- KAHHAPNRIQLSFT-UHFFFAOYSA-N 5-methoxypyrimidin-2-amine Chemical compound COC1=CN=C(N)N=C1 KAHHAPNRIQLSFT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IYMAUEAFOBSGCY-UHFFFAOYSA-N benzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=CC=C1 IYMAUEAFOBSGCY-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C1/00—Apparatus in which liquid or other fluent material is applied to the surface of the work by contact with a member carrying the liquid or other fluent material, e.g. a porous member loaded with a liquid to be applied as a coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C1/00—Apparatus in which liquid or other fluent material is applied to the surface of the work by contact with a member carrying the liquid or other fluent material, e.g. a porous member loaded with a liquid to be applied as a coating
- B05C1/04—Apparatus in which liquid or other fluent material is applied to the surface of the work by contact with a member carrying the liquid or other fluent material, e.g. a porous member loaded with a liquid to be applied as a coating for applying liquid or other fluent material to work of indefinite length
- B05C1/06—Apparatus in which liquid or other fluent material is applied to the surface of the work by contact with a member carrying the liquid or other fluent material, e.g. a porous member loaded with a liquid to be applied as a coating for applying liquid or other fluent material to work of indefinite length by rubbing contact, e.g. by brushes, by pads
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C5/00—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work
- B05C5/02—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work the liquid or other fluent material being discharged through an outlet orifice by pressure, e.g. from an outlet device in contact or almost in contact, with the work
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C9/00—Apparatus or plant for applying liquid or other fluent material to surfaces by means not covered by any preceding group, or in which the means of applying the liquid or other fluent material is not important
- B05C9/08—Apparatus or plant for applying liquid or other fluent material to surfaces by means not covered by any preceding group, or in which the means of applying the liquid or other fluent material is not important for applying liquid or other fluent material and performing an auxiliary operation
Description
Fremgangsmåte til fremstilling av 2-suHanUarnid-5-methoxy-pyrimidin. Process for the preparation of 2-sulfonamide-5-methoxy-pyrimidine.
Denne oppfinnelse angår en fremgangsmåte til fremstilling av 2-sulfanilamid-5-methoxy-pyrimidin med formelen: This invention relates to a process for the production of 2-sulfanilamide-5-methoxy-pyrimidine with the formula:
en kjemoterapeutisk. forbindelse med fordelaktige egenskaper, særlig en langvarig a chemotherapeutic. compound with beneficial properties, especially a long-lasting one
effektivitet i lave doser (Experimentia 17, effectiveness in low doses (Experimentia 17,
129, 1961; Arzneim. Forsen. 11, 681, og 682, 129, 1961; Arzneim. Too late. 11, 681, and 682,
1961). 1961).
Denne forbindelse kan fremstilles på This compound can be produced on
forskjellige måter, nemlig: a) ved å kondensere 2-amin-5-methoxy-pyrimidin med different ways, namely: a) by condensing 2-amine-5-methoxy-pyrimidine with
benzensulfoklorid som er substituert i p-stillingen med en aminogruppe eller en benzene sulphochloride which is substituted in the p-position with an amino group or a
gruppe som kan omdannes til aminogrup-pen, b) ved å kondensere 2-amino-5-meth-oxy-pyrimidin med p-nitrobenzen-sulfen-klorid eller p-acetamin-benzensulfin-klo-rid med påfølgende oxydasjon og reduk-sjon, eller hydrolyse av mellomproduktet, group that can be converted into the amino group, b) by condensing 2-amino-5-meth-oxy-pyrimidine with p-nitrobenzenesulfene chloride or p-acetamine benzenesulfine chloride with subsequent oxidation and reduction , or hydrolysis of the intermediate,
og c) ved å kondensere natriumsaltet av and c) by condensing the sodium salt off
sulfanilamid med 5-alkoxy-pyrimidyl-2-trimethyl-ammonium-jodid (tysk patent-skrift nr. 1 101 428). sulfanilamide with 5-alkoxy-pyrimidyl-2-trimethyl-ammonium iodide (German patent document no. 1 101 428).
Alle disse metoder er ufordelaktige, All these methods are disadvantageous,
fordi fremstillingen av utgangsmaterialene because the manufacture of the starting materials
er vanskelig og tidsspillende og er derfor is difficult and time-consuming and is therefore
uhensiktsmessig til å brukes i vanlig måle-stokk. unsuitable for use in a standard measuring stick.
Det har nu vist seg at 2-sulfanil-amid-5-methoxypyrimidinet kan oppnåes ved en It has now been shown that the 2-sulfanyl-amide-5-methoxypyrimidine can be obtained by a
ny metode som er å foretrekke. Denne er nærværende oppfinnelses formål. new method which is preferable. This is the purpose of the present invention.
Det vesentlige ved oppfinnelsen består i at en forbindelse med den generelle formel: The essence of the invention is that a compound with the general formula:
hvori R betyr et alkyl med 1—4 carbonatomer eller aralkyl først omdannes ved oxydasjon til en forbindelse med den generelle formel: hvori R har den samme betydning som i formel I, som derpå kondenseres med en forbindelse med den generelle formel in which R means an alkyl of 1-4 carbon atoms or aralkyl is first converted by oxidation to a compound of the general formula: in which R has the same meaning as in formula I, which is then condensed with a compound of the general formula
hvori X representerer -NH2-gruppen eller en rest som kan omdannes til -NHn-grup-pen, f. eks. til CH.,CONH-, C2H5OCONH-, eller -NO„, og Y representerer et hydrogenatom eller et alkalimetall-atom. in which X represents the -NH2 group or a residue that can be converted to the -NHn group, e.g. to CH.,CONH-, C2H5OCONH-, or -NO„, and Y represents a hydrogen atom or an alkali metal atom.
Kondenseringen kan utføres i nærvær av alkaliske reageringsmidler, f. eks. vann-frie alkalimetallcarbonater, eller i nærvær av overskytende alkalimetallsalt av stof-fet med den generelle formel III, f. eks. et sulfanilamid-natriumsalt. The condensation can be carried out in the presence of alkaline reactants, e.g. anhydrous alkali metal carbonates, or in the presence of excess alkali metal salt of the substance with the general formula III, e.g. a sulfanilamide sodium salt.
Ved utførelse av metoden ifølge oppfinnelsen kan oxydasjonen av forbindelsen med den generelle formel I til forbindelser med den generelle formel II utføres ved hjelp av forskjellige hensiktsmessige oxy-danter, f. eks. hydrogenperoxyd, natrium-hypoklorit, kaliumpermanganat, salpeter-syre og lignende, som regel i vandig eller surtvandig miljø. When carrying out the method according to the invention, the oxidation of the compound with the general formula I to compounds with the general formula II can be carried out with the help of various suitable oxidants, e.g. hydrogen peroxide, sodium hypochlorite, potassium permanganate, nitric acid and the like, usually in an aqueous or acidic environment.
Kondenseringsreaksjonen av forbindelsen med den generelle formel II med forbindelsen med den generelle formel III utføres ved bare å smelte begge komponen-ters blanding ved en temperatur på 80— 100°C, eller ved å opphete dem i et pas-sende oppløsningsmiddel eller i et smelte-befordrende middel, f. eks. dimethyl-form-amid, dimethyl-sulfoxyd, dialkyl-etere av ethylenglycol, urea og lignende. Da det derved dannede 2-sulfanilamid-5-meth-oxy-pyrimidin er mere surt enn kompo-nenten med den generelle formel III, dvs. det anvendte p-substituerte benzensulfon-amid, kan det tjene til å påskynne reaksjonen i nærvær av alkaliske reaksjonsmid-ler eller med overskytende alkalimetallsalt av det tilsvarende p-substituerte benzen-sulfonamid. Kondenseringen foregår me-get hurtig, uten at der oppstår biproduk-ter. The condensation reaction of the compound of the general formula II with the compound of the general formula III is carried out by simply melting the mixture of both components at a temperature of 80-100°C, or by heating them in a suitable solvent or in a melt - promoting agent, e.g. dimethylformamide, dimethylsulfoxide, dialkyl ethers of ethylene glycol, urea and the like. As the 2-sulfanilamide-5-methoxy-pyrimidine thus formed is more acidic than the component with the general formula III, i.e. the p-substituted benzenesulfonamide used, it can serve to accelerate the reaction in the presence of alkaline reagents or with excess alkali metal salt of the corresponding p-substituted benzene sulfonamide. Condensation takes place very quickly, without by-products arising.
Sammenlignet med de foran omtalte metoder medfører fremgangsmåten ifølge oppfinnelsen en rekke fordeler. Fremfor alt er utgangsmaterialene lett tilgjenge-lige, mellomprodukter har fordelaktige fysikalsk-kjemiske egenskaper, så at de lett kan isoleres, reaksjonen forløper glatt, med enkle apparater, og der oppnås store ut-bytter. Compared to the methods mentioned above, the method according to the invention entails a number of advantages. Above all, the starting materials are readily available, intermediate products have advantageous physico-chemical properties, so that they can be easily isolated, the reaction proceeds smoothly, with simple apparatus, and large yields are obtained.
Eksempel 1. Example 1.
En blanding av 10 ml iseddiksyre og 5 ml 30 pst. hydrogenperoxyd tilsettes under omrøring 3,4 g 2-ethylmercapto-5-meth-oxy-pyrimidin. Når den exotermiske reak-sjon er avsluttet opphetes reaksjonsblan-dingen i en time til 80 °C hvoretter den konsentreres for å krystallisere. Det oppnådde produkt suges ut, vaskes og tørres ved 75—76°C. A mixture of 10 ml of glacial acetic acid and 5 ml of 30% hydrogen peroxide is added with stirring to 3.4 g of 2-ethylmercapto-5-meth-oxy-pyrimidine. When the exothermic reaction has ended, the reaction mixture is heated for one hour to 80 °C, after which it is concentrated to crystallize. The product obtained is sucked out, washed and dried at 75-76°C.
2,2 g av det således oppnådde 2-ethyl-sulfonyl-5-methoxy pyrimidin blandes omhyggelig med 4 g sulfanilamidnatriumsalt og opphetes til 80—100 °C hvorved reak-sjonsblandingen blir flytende, og temperaturen økes til 130—150°C. Efter nedkjøl-ing blir den oppnådde faste smelte malt med 20 ml vann, den uoppløselige del suget 2.2 g of the thus obtained 2-ethyl-sulfonyl-5-methoxy pyrimidine is carefully mixed with 4 g of sulfanilamide sodium salt and heated to 80-100 °C, whereby the reaction mixture becomes liquid, and the temperature is increased to 130-150 °C. After cooling, the obtained solid melt is ground with 20 ml of water, the insoluble part is sucked
av og vasket med vann. Filtratet blir i het tilstand innstilt på pH-verdi 5—7 ved tilsetning av saltsyre. Det eliminerte 2-sulfanilamid-5-methoxy-pyrimidin suges ut og vaskes med vann. Efter krystallisering fra 50 pst. ethanol har det smeltepunkt 211— 212°C. off and washed with water. In a hot state, the filtrate is adjusted to a pH value of 5-7 by adding hydrochloric acid. The eliminated 2-sulfanilamide-5-methoxy-pyrimidine is sucked off and washed with water. After crystallization from 50% ethanol, it has a melting point of 211-212°C.
Eksempel 2. Example 2.
En suspensjon av 15,6 g 2-methylen-mercapto-5-methoxy-pyrimidin i 25 ml vann tilsettes dråpevis under omrøring 350 ml av en oppløsning av natriumhypo-klorit som inneholder 14,9 g NaOCl, hvor efter temperaturen ved utvendig avkjøling med isvann holdes på 0—10°C. Efter at ut-gangsstoffet imens er oppløst, uttappes det dannede 2-methylsulfonyl-5-methoxy-pyrimidin. Når reaksjonen er ferdig, suges det oppnådde produkt ut, vaskes og tørres. Utbyttet er 15,0 g, dvs. 80 pst. Ved å konsen-trere moderluten kan der utvinnes dess-uten 2,4 g av stoffet, så at der oppnås ialt 17,4 g, dvs. 92,5 pst. Smeltepunkt 113— 115°C. A suspension of 15.6 g of 2-methylene-mercapto-5-methoxy-pyrimidine in 25 ml of water is added dropwise with stirring to 350 ml of a solution of sodium hypochlorite containing 14.9 g of NaOCl, where after the temperature on external cooling with ice water is kept at 0-10°C. After the starting material has meanwhile dissolved, the 2-methylsulfonyl-5-methoxy-pyrimidine formed is drawn off. When the reaction is finished, the product obtained is sucked out, washed and dried. The yield is 15.0 g, i.e. 80 per cent. By concentrating the mother liquor, an additional 2.4 g of the substance can be recovered, so that a total of 17.4 g, i.e. 92.5 per cent, is obtained. Melting point 113 — 115°C.
3,76 g av det således oppnådde 2-met-hylensulfohyl-5-methoxy-pyrimidin opphetes med 8,55 g sulfanilamidnatriumsalt i 10 ml dimethylformamid i iy2 time til 100 —105°C. Efter nedkjøling fortynnes reak-sjonsblandingen med 20 ml vann og nøtra-liseres med fortynnet HC1. Den således oppnådde blanding av sulfanilamid og 2-sulfanilamid-5-methoxypyrimidin avsuges, utkokes med 20 ml vann, avsuges igjen og vaskes omhyggelig med vann. Utbyttet er 4,2 g, dvs. 75 pst. Av moderluten utvinnes sulfanilamid ved krystallisering. 3.76 g of the thus obtained 2-methylenesulfoyl-5-methoxy-pyrimidine is heated with 8.55 g of sulfanilamide sodium salt in 10 ml of dimethylformamide for 1y2 hours to 100-105°C. After cooling, the reaction mixture is diluted with 20 ml of water and neutralized with dilute HCl. The thus obtained mixture of sulfanilamide and 2-sulfanilamide-5-methoxypyrimidine is filtered off, boiled with 20 ml of water, filtered again and washed carefully with water. The yield is 4.2 g, i.e. 75 per cent. From the mother liquor, sulfanilamide is recovered by crystallization.
Eksempel 3. Example 3.
5,1 g 2-ethylmercapto-5-methoxy-pyrimidin (smeltepunkt 33,5—34,5°C) sus-penderes i 145 ml vann. Derefter blir ved 5—10°C tilsatt dråpevis i løpet av 10 minutter og under omrøring 55 ml oppløsning av natrium-hypoklorit med innhold 0,06 mol NaOCl. Temperaturen økes derefter til 20° C, og blandingen omrøres i 2 timer. Den således dannede oppløsning inndampes i vakuum for å krystalliseres. Der oppnås 5,5 g av 2-ethyl-sulfonyl-5-methoxypyri-midin med smeltepunkt 74—75°C. Efter vaskning med vann og krystallisering er smeltepunktet 75—76,5°C. 5.1 g of 2-ethylmercapto-5-methoxy-pyrimidine (melting point 33.5-34.5°C) is suspended in 145 ml of water. Then, at 5-10°C, 55 ml of a solution of sodium hypochlorite with a content of 0.06 mol of NaOCl is added dropwise over 10 minutes and with stirring. The temperature is then increased to 20° C., and the mixture is stirred for 2 hours. The solution thus formed is evaporated in vacuum to crystallize. There, 5.5 g of 2-ethyl-sulfonyl-5-methoxypyrimidine with a melting point of 74-75°C are obtained. After washing with water and crystallization, the melting point is 75-76.5°C.
En blanding av 1,0 g 2-ethylsulfonyl-5-methoxypyrimidin og 2,18 g sulfanilamid-natriumsalt opphetes under omrøring først i 15 minutter til 110—120°C og derefter i 1 time til 158—165°C. Efter delvis avkjøling oppløses smeiten i 6 ml hett vann. Efter fullstendig nedkjøling blir bunnfallet (ureagert sulfanilamid) avsuget og vasket med vann. De forenede filtrater syres med fortynnet HC1 til pH-verdi 5. Det således dannede bunnfall suges ut, vaskes med vann og utkokes derefter med 25 ml vann. Det oppnådde 2-sulfanilamid-5-methoxy-pyrimidin renses ved bunnfelling med HC1 fra en ammoniakalsk oppløsning. Utbyttet er 0,56 g med smeltepunkt 210—212°C. A mixture of 1.0 g of 2-ethylsulfonyl-5-methoxypyrimidine and 2.18 g of sulfanilamide sodium salt is heated with stirring first for 15 minutes to 110-120°C and then for 1 hour to 158-165°C. After partial cooling, the mixture is dissolved in 6 ml of hot water. After complete cooling, the precipitate (unreacted sulfanilamide) is suctioned off and washed with water. The combined filtrates are acidified with diluted HCl to a pH value of 5. The precipitate thus formed is suctioned off, washed with water and then boiled off with 25 ml of water. The 2-sulfanilamide-5-methoxy-pyrimidine obtained is purified by precipitation with HCl from an ammoniacal solution. The yield is 0.56 g with a melting point of 210-212°C.
Eksempel 4. Example 4.
5,6 g 2-benzylmercapto-5-methoxy-pyrimidin (smeltepunkt 47—49°C) suspende-res i 210 ml vann ved en temperatur på 0—5°C og 42 ml natrium-hypoklorit-opp-løsning med innhold 0,048 mol NaOCl tilsettes langsomt. Derefter økes temperaturen til 20°C og blandingen omrøres i 10— 20 timer ved romtemperatur. Det oppnådde produkt suges ut, vaskes med vann og lufttørres. Utbyttet 2-benzylsulfonyl-5-methoxy pyrimidin er 5,2 g, og efter krystallisering fra 80 pst.-ethanol er smeltepunktet 110—112°C. 5.6 g of 2-benzylmercapto-5-methoxy-pyrimidine (melting point 47-49°C) is suspended in 210 ml of water at a temperature of 0-5°C and 42 ml of sodium hypochlorite solution with a content of 0.048 mol NaOCl is added slowly. The temperature is then increased to 20°C and the mixture is stirred for 10-20 hours at room temperature. The product obtained is extracted, washed with water and air-dried. The yield of 2-benzylsulfonyl-5-methoxy pyrimidine is 5.2 g, and after crystallization from 80% ethanol the melting point is 110-112°C.
En blanding av 1,32 g 2-benzylsulfo-nyl-5-methoxypyrimidin og 4,4 g sulfanilamid natriumsalt opphetes i 30 minutter under omrøring til en temperatur på 155— 165°C og holdes på den samme temperatur i 1 time til. Smeiten blir derefter ned-kjølt til 120°C og oppløses ved tilsetning av 6 ml varmt vann. Den oppnådde oppløs-ning innstilles på pH-verdi 9, og det således fraskilte bunnfall (ureagert sulfanilamid) utsuges. Filtratet opphetes til 50—100°C og syres med fortynnet HC1 til pH-verdi 5. Det dannede rå 2-sulfanilamid-5-methoxy-pyrimidin suges ut og utkokes med 30 ml vann. Derefter renses det ved ny bunnfelling fra ammoniakalsk oppløsning ved hjelp av HC1. Utbyttet er 0,35 g med smeltepunkt 209,5—212°C. A mixture of 1.32 g of 2-benzylsulfonyl-5-methoxypyrimidine and 4.4 g of sulfanilamide sodium salt is heated for 30 minutes with stirring to a temperature of 155-165°C and kept at the same temperature for 1 hour more. The melt is then cooled to 120°C and dissolved by adding 6 ml of hot water. The obtained solution is adjusted to a pH value of 9, and the thus separated precipitate (unreacted sulfanilamide) is suctioned off. The filtrate is heated to 50-100°C and acidified with dilute HCl to a pH value of 5. The crude 2-sulfanilamide-5-methoxy-pyrimidine formed is suctioned off and boiled with 30 ml of water. It is then purified by re-precipitation from an ammoniacal solution using HC1. The yield is 0.35 g with a melting point of 209.5-212°C.
Eksempel 5. Example 5.
En blanding av 8,5 g N4-acetylsulfanil-amid, 7,5 g 2-methyl-sulfonyl-5-methoxy pyrimidin og 5,5 g friskt kalsinert pottaske opphetes langsomt under omrøring til temperaturen 130°C, og omrøringen fortsettes i iy2 time ved 130—140°C. Reaksjonsblan-dingen avkjøles litt og oppløses i hett vann og nøytraliseres med HC1. Det dannede produkt suges av, opphetes til kokning med 100 ml vann, suges ut igjen mens det er hett og vaskes med vann. Efterat de forenede filtrater var avkjølt, utkrystalliseres det ureagerte N4-acetylsulfanilamid. Den i hett vann uoppløselige del forsåpes ved 1 times kokning med 80 ml 2N-NaOH. Den fortsatte hete oppløsning nøytraliseres med fortynnet saltsyre, og det således eliminerte 2-sulfanilamid-5-methoxy-pyrimidin utsuges, vaskes og tørres. Utbyttet er 5,2 g med smeltepunkt 211—212°C. A mixture of 8.5 g of N4-acetylsulfanylamide, 7.5 g of 2-methyl-sulfonyl-5-methoxy pyrimidine and 5.5 g of freshly calcined pot ash is slowly heated with stirring to a temperature of 130°C, and the stirring is continued for iy2 hour at 130-140°C. The reaction mixture is cooled slightly and dissolved in hot water and neutralized with HC1. The product formed is sucked off, heated to boiling with 100 ml of water, sucked off again while hot and washed with water. After the combined filtrates have cooled, the unreacted N4-acetylsulfanilamide crystallizes out. The part insoluble in hot water is saponified by boiling for 1 hour with 80 ml of 2N-NaOH. The continued hot solution is neutralized with dilute hydrochloric acid, and the thus eliminated 2-sulfanilamide-5-methoxy-pyrimidine is extracted, washed and dried. The yield is 5.2 g with a melting point of 211-212°C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7536724A FR2333583A1 (en) | 1975-12-01 | 1975-12-01 | DEVICE FOR APPLYING A COATING TO A SUBMERSIBLE SURFACE |
| FR7632205A FR2369010A2 (en) | 1976-10-26 | 1976-10-26 | Underwater paint applicator - with paint distributor moving along and pressed against surface and displacing water from surface |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO764073L NO764073L (en) | 1977-06-02 |
| NO149027B true NO149027B (en) | 1983-10-24 |
| NO149027C NO149027C (en) | 1984-02-01 |
Family
ID=26219170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO764073A NO149027C (en) | 1975-12-01 | 1976-11-29 | DEVICE FOR AA APPLYING A COAT ON A DOWN SURFACE |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6012098B2 (en) |
| AU (1) | AU498056B2 (en) |
| DE (1) | DE2654328A1 (en) |
| ES (1) | ES453789A1 (en) |
| GB (1) | GB1517239A (en) |
| IT (1) | IT1072111B (en) |
| NL (1) | NL7613400A (en) |
| NO (1) | NO149027C (en) |
| PT (1) | PT65893B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3912782A1 (en) * | 1989-04-19 | 1990-10-25 | Bayerische Motoren Werke Ag | Nozzle applying adhesive or sealing compound - has step formed on nozzle end face to control thickness of compound |
| DE102019134132A1 (en) * | 2019-12-12 | 2021-06-17 | Mankiewicz Gebr. & Co (Gmbh & Co Kg) | Device and method for the production of edge protection coatings |
| RU2753409C1 (en) * | 2020-11-09 | 2021-08-16 | Владимир Васильевич Касаткин | Surface coating device, non-contact with coating substance |
| CN115025927B (en) * | 2022-05-25 | 2024-01-12 | 青岛优梦家居科技有限公司 | Resin finishing equipment for cloth textile dyeing and finishing with leveling function |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1900089A1 (en) * | 1969-01-02 | 1970-11-12 | Leopold Krueger | Device for producing a paint, in particular an underwater paint |
| IT957249B (en) * | 1972-03-08 | 1973-10-10 | Lodi F | EQUIPMENT FOR CLEANING SURFACES SUBMERSIBLE BY OR GANIC FORMATIONS IN SPECIES FOR NA TANT HULLS |
-
1976
- 1976-11-26 PT PT65893A patent/PT65893B/en unknown
- 1976-11-29 NO NO764073A patent/NO149027C/en unknown
- 1976-11-30 AU AU20104/76A patent/AU498056B2/en not_active Expired
- 1976-11-30 IT IT69856/76A patent/IT1072111B/en active
- 1976-11-30 DE DE19762654328 patent/DE2654328A1/en not_active Ceased
- 1976-11-30 ES ES453789A patent/ES453789A1/en not_active Expired
- 1976-12-01 JP JP51143523A patent/JPS6012098B2/en not_active Expired
- 1976-12-01 GB GB50111/76A patent/GB1517239A/en not_active Expired
- 1976-12-01 NL NL7613400A patent/NL7613400A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5266549A (en) | 1977-06-02 |
| ES453789A1 (en) | 1977-12-16 |
| AU498056B2 (en) | 1979-02-01 |
| NL7613400A (en) | 1977-06-03 |
| IT1072111B (en) | 1985-04-10 |
| GB1517239A (en) | 1978-07-12 |
| AU2010476A (en) | 1978-06-08 |
| NO764073L (en) | 1977-06-02 |
| DE2654328A1 (en) | 1977-06-08 |
| PT65893B (en) | 1978-05-18 |
| NO149027C (en) | 1984-02-01 |
| PT65893A (en) | 1976-12-01 |
| JPS6012098B2 (en) | 1985-03-29 |
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