GB595965A - Improvements relating to the manufacture of amidines - Google Patents
Improvements relating to the manufacture of amidinesInfo
- Publication number
- GB595965A GB595965A GB1773245A GB1773245A GB595965A GB 595965 A GB595965 A GB 595965A GB 1773245 A GB1773245 A GB 1773245A GB 1773245 A GB1773245 A GB 1773245A GB 595965 A GB595965 A GB 595965A
- Authority
- GB
- United Kingdom
- Prior art keywords
- heated
- thiocyanate
- product
- converted
- picrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001409 amidines Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N Ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 239000000243 solution Substances 0.000 abstract 6
- FARXIDYHJAANGP-UHFFFAOYSA-N 4-methylsulfonylbenzonitrile Chemical compound CS(=O)(=O)C1=CC=C(C#N)C=C1 FARXIDYHJAANGP-UHFFFAOYSA-N 0.000 abstract 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 3
- 239000012458 free base Substances 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 229940075930 picrate Drugs 0.000 abstract 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N Picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 2
- SPEMTLAMABUSQQ-UHFFFAOYSA-M [S-]C#N.CNC Chemical compound [S-]C#N.CNC SPEMTLAMABUSQQ-UHFFFAOYSA-M 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 230000001476 alcoholic Effects 0.000 abstract 2
- CLFAPTXAJGBEMW-UHFFFAOYSA-J azane;chromium(3+);tetrathiocyanate Chemical compound N.N.[Cr+3].[S-]C#N.[S-]C#N.[S-]C#N.[S-]C#N CLFAPTXAJGBEMW-UHFFFAOYSA-J 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 abstract 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 2
- 229940114148 picric acid Drugs 0.000 abstract 2
- 229950002929 trinitrophenol Drugs 0.000 abstract 2
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 abstract 1
- VWPJXEYDYJQMBC-UHFFFAOYSA-N 3-methylsulfonylbenzonitrile Chemical compound CS(=O)(=O)C1=CC=CC(C#N)=C1 VWPJXEYDYJQMBC-UHFFFAOYSA-N 0.000 abstract 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 abstract 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 abstract 1
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 abstract 1
- -1 Amidine thiocyanates Chemical class 0.000 abstract 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N Benzyl cyanide Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 1
- BAABOMKQBNGZTB-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)O.CNC(C1=CC=C(C=C1)S(=O)(=O)C)=N Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.CNC(C1=CC=C(C=C1)S(=O)(=O)C)=N BAABOMKQBNGZTB-UHFFFAOYSA-N 0.000 abstract 1
- TWZHKUJTFMFCAD-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C(C1=CC=CC=C1)(=N)N Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C(C1=CC=CC=C1)(=N)N TWZHKUJTFMFCAD-UHFFFAOYSA-N 0.000 abstract 1
- SXLBFGVKRDDTNK-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C(CCCCCCC)(=N)N Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C(CCCCCCC)(=N)N SXLBFGVKRDDTNK-UHFFFAOYSA-N 0.000 abstract 1
- OOJPVJZTGVWMSH-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C(N)(=N)C1=NC=CC=C1 Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C(N)(=N)C1=NC=CC=C1 OOJPVJZTGVWMSH-UHFFFAOYSA-N 0.000 abstract 1
- TVYYXOJXVFUONC-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1(=CC=CC=C1)CC(=N)N Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1(=CC=CC=C1)CC(=N)N TVYYXOJXVFUONC-UHFFFAOYSA-N 0.000 abstract 1
- HECHGEULHSNZLQ-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1=C(C=CC2=CC=CC=C12)C(=N)N Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1=C(C=CC2=CC=CC=C12)C(=N)N HECHGEULHSNZLQ-UHFFFAOYSA-N 0.000 abstract 1
- RWALYVZZSHQRJP-UHFFFAOYSA-N N'-benzyl-4-methylsulfonylbenzenecarboximidamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=N)NCC1=CC=CC=C1 RWALYVZZSHQRJP-UHFFFAOYSA-N 0.000 abstract 1
- KATOTACQUVLLMV-UHFFFAOYSA-N O.O.NC(=N)C1=CC=C(O)C=C1 Chemical compound O.O.NC(=N)C1=CC=C(O)C=C1 KATOTACQUVLLMV-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N Thiocyanic acid Chemical class SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- AJQZICDKYRHORR-UHFFFAOYSA-M [S-]C#N.BrC1=CC=C(C(=N)N)C=C1 Chemical compound [S-]C#N.BrC1=CC=C(C(=N)N)C=C1 AJQZICDKYRHORR-UHFFFAOYSA-M 0.000 abstract 1
- IHHYYBHWNAIJPZ-UHFFFAOYSA-M [S-]C#N.C(C1=CC=CC=C1)N Chemical compound [S-]C#N.C(C1=CC=CC=C1)N IHHYYBHWNAIJPZ-UHFFFAOYSA-M 0.000 abstract 1
- ZVCMGZSMACGTPA-UHFFFAOYSA-M [S-]C#N.CN Chemical compound [S-]C#N.CN ZVCMGZSMACGTPA-UHFFFAOYSA-M 0.000 abstract 1
- DSACVZDNNCNLMA-UHFFFAOYSA-M [S-]C#N.CS(=O)(=O)C=1C=C(C(=N)N)C=CC1 Chemical compound [S-]C#N.CS(=O)(=O)C=1C=C(C(=N)N)C=CC1 DSACVZDNNCNLMA-UHFFFAOYSA-M 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000005418 aryl aryl group Chemical group 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- NWSUEGIXYXLCIR-UHFFFAOYSA-N hydron;4-methylsulfonylbenzenecarboximidamide;chloride Chemical compound Cl.CS(=O)(=O)C1=CC=C(C(N)=N)C=C1 NWSUEGIXYXLCIR-UHFFFAOYSA-N 0.000 abstract 1
- AZKDTTQQTKDXLH-UHFFFAOYSA-N naphthalene-2-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- YSIMAPNUZAVQER-UHFFFAOYSA-N octanenitrile Chemical compound CCCCCCCC#N YSIMAPNUZAVQER-UHFFFAOYSA-N 0.000 abstract 1
- HHUXWFCTZRENLW-UHFFFAOYSA-N piperidin-1-ium;thiocyanate Chemical compound SC#N.C1CCNCC1 HHUXWFCTZRENLW-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- ZVUUCUFDAHKLKT-UHFFFAOYSA-M sodium;2,4,6-trinitrophenolate Chemical compound [Na+].[O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZVUUCUFDAHKLKT-UHFFFAOYSA-M 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Amidine thiocyanates of the general formula <FORM:0595965/IV/1> wherein R represents an alkyl, aryl or substituted aryl, aralkyl, alicyclic or heterocyclic group, and R1 and R2 each represent hydrogen or an alkyl or aralkyl radical or together form an alkylene chain, are manufactured by heating a nitrile R.CN at about 180-240 DEG C., if desired in the presence of a solvent, with ammonium thiocyanate, thiourea, a thiocyanic acid salt of a monoamine NHR1R2, or an unsymmetrical alkylthiourea. The products may be converted into the free amidines, and salts with other acids may be prepared from the latter, or, in some cases, by adding the appropriate acid to a solution of the thiocyanate. In examples: (1) heptyl cyanide is heated with ammonium thiocyanate and the product is treated with aqueous sodium hydroxide, extracted with ether and the ethereal solution mixed with an alcoholic picric acid solution to form caprylamidine picrate; (2) phenylacetamidine picrate is prepared from benzyl cyanide as in (1), except that chloroform is used for the extraction; (3) benzamidine picrate is prepared from benzonitrile as in (2); (4) p-bromobenzonitrile is heated with ammonium thiocyanate to produce p-bromobenzamidine thiocyanate; (5) as in (4), but with conversion of the thiocyanate to the picrate by treating an aqueous solution of the former with an alcoholic picric acid solution; (6) p-cyanophenol is heated with ammonium thiocyanate and the product is treated with aqueous ammonia to liberate p-hydroxybenzamidine dihydrate; (7) anisonitrile is heated with ammonium thiocyanate and anioamidine is liberated by means of aqueous sodium hydroxide solution, dissolved in dilute hydrochloric acid, and sodium picrate solution is added, producing anioamidine picrate; (8) p-cyanophenyl methyl sulphone is heated with ammonium thiocyanate, if desired in the presence of glycerol, or with thiourea, and the product is converted into p-amidinophenyl methyl sulphone hydrochloride via the free base; (a) m-methylsulphonylbenzonitrile is heated with ammonium thiocyanate to give m - methylsulphonylbenzamidine thiocyanate; (10) p-sulphamidobenzonitrile is heated with ammonium thiocyanate and the product is converted to p-sulphamidobenzamidine hydrochloride; (11) p-cyanophenyl methyl sulphone is heated with benzylamine thiocyanate and the product is converted to N-benzyl-p-methylsulphonylbenzamidine reineckate via the free base and its hydrochloride; (12) benzonitrile is heated with piperidine thiocyanate and the product is converted to N : N-pentamethylenebenzamidine picrate; (13) benzonitrile is heated with dimethylamine thiocyanate, and the product is converted to N : N-dimethylbenzamidine reineckate via the hydrochloride, the free base and its benzenesulphonate; (14) p-methylsulphonylbenzonitrile is heated with dimethylamine thiocyanate, and the product is converted to N : N - dimethyl - p - methylsulphonylbenz - amidine; (15) p-methylsulphonylbenzonitrile is heated with methylamine thiocyanate and the product is converted to N-methyl-p-methylsulphonylbenzamidine benzenesulphonate; (16) 2-naphthonitrile is heated with ammonium thiocyanate or thiourea and the product is converted to 2-naphthamidine picrate; (17) 2-cyanopyridine is heated with ammonium thiocyanate and the product is converted to 2-amidinopyridine picrate; (18) 4 : 41-dicyano-a : g -diphenoxypropane is heated with ammonium thiocyanate and the product is converted to 4 : 41 - diamidino - a : g - diphenoxypropane hydrochloride; (19) p : p1 - dicyanodiphenyl ether similarly yields p : p1-diamidinodiphenyl ether dihydrochloride dihydrate; (20) 4 : 41-dicyanostilbene similarly yields 4 : 41-diamidinostilbene dihydrochloride dihydrate.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595965A true GB595965A (en) | 1947-12-23 |
Family
ID=1733360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1773245A Expired GB595965A (en) | 1945-07-11 | Improvements relating to the manufacture of amidines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595965A (en) |
-
1945
- 1945-07-11 GB GB1773245A patent/GB595965A/en not_active Expired
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