DD143256A5 - Verfahren zur herstellung von n-cyano-n'-methyl-n"-(2-eckige klammer auf (4-methyl-5-imidazolyl)-methylthio eckige klammer zu -aethyl)-guanidin - Google Patents
Verfahren zur herstellung von n-cyano-n'-methyl-n"-(2-eckige klammer auf (4-methyl-5-imidazolyl)-methylthio eckige klammer zu -aethyl)-guanidin Download PDFInfo
- Publication number
- DD143256A5 DD143256A5 DD79212494A DD21249479A DD143256A5 DD 143256 A5 DD143256 A5 DD 143256A5 DD 79212494 A DD79212494 A DD 79212494A DD 21249479 A DD21249479 A DD 21249479A DD 143256 A5 DD143256 A5 DD 143256A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- cyano
- ethyl
- guanidine
- imidazolyl
- Prior art date
Links
- -1 (4-METHYL-5-IMIDAZOLYL) -METHYLTHIO Chemical class 0.000 title claims description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 230000002051 biphasic effect Effects 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 239000011435 rock Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000011097 chromatography purification Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- CYNUYVMHFCEMJY-UHFFFAOYSA-N 1-ethyl-2-(5-methyl-1H-imidazol-4-yl)-1-methylsulfanylguanidine Chemical compound CC1=C(N=CN1)N=C(N(CC)SC)N CYNUYVMHFCEMJY-UHFFFAOYSA-N 0.000 description 1
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- PDWPOXKSTFGRIT-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole;hydrochloride Chemical compound Cl.CC=1NC=NC=1CCl PDWPOXKSTFGRIT-UHFFFAOYSA-N 0.000 description 1
- NOIIXXUKYRYBRT-UHFFFAOYSA-N 5-(chloromethyl)-4-ethyl-1h-imidazole Chemical compound CCC=1NC=NC=1CCl NOIIXXUKYRYBRT-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- XMYLSWOTJKUSHE-UHFFFAOYSA-N cyanamide;lead Chemical compound [Pb].NC#N XMYLSWOTJKUSHE-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU998/78A YU40332B (en) | 1978-04-26 | 1978-04-26 | Process for preparing n-cyano-n'-methyl-n''-((2-((4-methyl-5-imidazolyl)-methylthio)ethyl)-guanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD143256A5 true DD143256A5 (de) | 1980-08-13 |
Family
ID=25552339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79212494A DD143256A5 (de) | 1978-04-26 | 1979-04-25 | Verfahren zur herstellung von n-cyano-n'-methyl-n"-(2-eckige klammer auf (4-methyl-5-imidazolyl)-methylthio eckige klammer zu -aethyl)-guanidin |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4200761A (cs) |
| JP (1) | JPS5440547B1 (cs) |
| AR (1) | AR219794A1 (cs) |
| AT (1) | AT363956B (cs) |
| BE (1) | BE875845A (cs) |
| CA (2) | CA1121363A (cs) |
| CS (1) | CS203037B2 (cs) |
| DD (1) | DD143256A5 (cs) |
| DE (1) | DE2916610C2 (cs) |
| ES (1) | ES479925A1 (cs) |
| FR (1) | FR2424261A1 (cs) |
| GB (2) | GB2041362B (cs) |
| HU (1) | HU180830B (cs) |
| IT (1) | IT1165198B (cs) |
| PL (1) | PL115342B1 (cs) |
| PT (1) | PT69542A (cs) |
| RO (1) | RO78325A (cs) |
| SU (1) | SU862822A3 (cs) |
| YU (1) | YU40332B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6056139B2 (ja) * | 1980-11-26 | 1985-12-09 | 藤本製薬株式会社 | シアノグアニジン誘導体の製造法 |
| CN111848458B (zh) * | 2020-08-05 | 2022-04-26 | 原平市同利化工有限责任公司 | 一种制备3-巯基丙酸的过程中提取双氰胺的工艺 |
| CN115784940B (zh) * | 2022-12-07 | 2023-12-05 | 内蒙古欣皓医药科技有限公司 | 一种双氰胺晶体的结晶方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| US4025527A (en) * | 1973-07-13 | 1977-05-24 | Smith Kline & French Laboratories Limited | Certain thiazoles and oxazoles |
| GB1533380A (en) * | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
| GB1531231A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for the production of cyanoguanidine derivatives |
| US4112234A (en) * | 1977-08-22 | 1978-09-05 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
| CH631971A5 (en) * | 1977-12-30 | 1982-09-15 | Crc Ricerca Chim | Process for preparing imidazole derivatives |
-
1978
- 1978-04-26 YU YU998/78A patent/YU40332B/xx unknown
-
1979
- 1979-04-17 AT AT0282779A patent/AT363956B/de not_active IP Right Cessation
- 1979-04-18 US US06/031,239 patent/US4200761A/en not_active Expired - Lifetime
- 1979-04-20 GB GB8000974A patent/GB2041362B/en not_active Expired
- 1979-04-20 GB GB7913760A patent/GB2019842B/en not_active Expired
- 1979-04-24 IT IT67876/79A patent/IT1165198B/it active
- 1979-04-24 AR AR276281A patent/AR219794A1/es active
- 1979-04-24 PT PT69542A patent/PT69542A/pt unknown
- 1979-04-24 CA CA000326202A patent/CA1121363A/en not_active Expired
- 1979-04-24 JP JP4983679A patent/JPS5440547B1/ja active Pending
- 1979-04-24 DE DE2916610A patent/DE2916610C2/de not_active Expired
- 1979-04-24 RO RO7997352A patent/RO78325A/ro unknown
- 1979-04-25 DD DD79212494A patent/DD143256A5/de not_active IP Right Cessation
- 1979-04-25 SU SU792760898A patent/SU862822A3/ru active
- 1979-04-25 ES ES479925A patent/ES479925A1/es not_active Expired
- 1979-04-25 CS CS792885A patent/CS203037B2/cs unknown
- 1979-04-25 BE BE0/194829A patent/BE875845A/xx not_active IP Right Cessation
- 1979-04-26 HU HU79LE840A patent/HU180830B/hu not_active IP Right Cessation
- 1979-04-26 PL PL1979215185A patent/PL115342B1/pl unknown
- 1979-04-26 FR FR7910594A patent/FR2424261A1/fr active Granted
-
1985
- 1985-09-24 CA CA000491471A patent/CA1209153B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1209153B (en) | 1986-08-05 |
| BE875845A (fr) | 1979-08-16 |
| FR2424261A1 (fr) | 1979-11-23 |
| GB2019842A (en) | 1979-11-07 |
| PL215185A1 (cs) | 1980-01-28 |
| ATA282779A (de) | 1981-02-15 |
| PT69542A (en) | 1979-05-01 |
| DE2916610A1 (de) | 1979-10-31 |
| RO78325A (ro) | 1982-04-12 |
| AR219794A1 (es) | 1980-09-15 |
| FR2424261B1 (cs) | 1983-05-13 |
| YU99878A (en) | 1982-10-31 |
| SU862822A3 (ru) | 1981-09-07 |
| JPS5440547B1 (cs) | 1979-12-04 |
| IT7967876A0 (it) | 1979-04-24 |
| DE2916610C2 (de) | 1986-04-03 |
| AT363956B (de) | 1981-09-10 |
| US4200761A (en) | 1980-04-29 |
| ES479925A1 (es) | 1979-12-01 |
| IT1165198B (it) | 1987-04-22 |
| CS203037B2 (en) | 1981-02-27 |
| PL115342B1 (en) | 1981-03-31 |
| GB2041362B (en) | 1982-08-18 |
| YU40332B (en) | 1985-12-31 |
| CA1121363A (en) | 1982-04-06 |
| GB2041362A (en) | 1980-09-10 |
| HU180830B (en) | 1983-04-29 |
| GB2019842B (en) | 1982-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |