DE2944257A1 - Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl) guanidin - Google Patents
Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl) guanidinInfo
- Publication number
- DE2944257A1 DE2944257A1 DE19792944257 DE2944257A DE2944257A1 DE 2944257 A1 DE2944257 A1 DE 2944257A1 DE 19792944257 DE19792944257 DE 19792944257 DE 2944257 A DE2944257 A DE 2944257A DE 2944257 A1 DE2944257 A1 DE 2944257A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- guanidine
- cyano
- dithiobisethyl
- mol
- 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.)
- Withdrawn
Links
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
- 229960003151 mercaptamine Drugs 0.000 claims description 4
- MHGGQXIPBPGZFB-UHFFFAOYSA-N methyl n-cyano-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NC#N MHGGQXIPBPGZFB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZORWZOOZJGMSTE-UHFFFAOYSA-N 1-cyano-2-methyl-3-(2-sulfanylethyl)guanidine Chemical compound N#CNC(=NC)NCCS ZORWZOOZJGMSTE-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU255178A YU41127B (en) | 1978-11-02 | 1978-11-02 | Process for obtaining n-cyano-n-methyl-n-(2-mercaptoethyl)-guanidine |
| YU36579A YU41615B (en) | 1979-02-15 | 1979-02-15 | Process for obtaining n-cyano-n-methyl-n"-(2-mercaptoethyl)-quanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2944257A1 true DE2944257A1 (de) | 1980-05-14 |
Family
ID=27130733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792944257 Withdrawn DE2944257A1 (de) | 1978-11-02 | 1979-11-02 | Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl) guanidin |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT368991B (it) |
| CH (1) | CH645098A5 (it) |
| DE (1) | DE2944257A1 (it) |
| GB (1) | GB2035313B (it) |
| IT (1) | IT1192784B (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2528833A1 (fr) * | 1982-06-16 | 1983-12-23 | May & Baker Ltd | Derives de la cystamine, leur preparation et les compositions comme facteur de croissance qui les contiennent |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0623179B2 (ja) * | 1986-09-01 | 1994-03-30 | 三井石油化学工業株式会社 | シアノグアニジン誘導体及びその製造法 |
| JPH0623180B2 (ja) * | 1987-02-17 | 1994-03-30 | 三井石油化学工業株式会社 | シアノグアニジン誘導体及びその製造法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7510344A (nl) * | 1974-09-02 | 1976-03-04 | Smith Kline French Lab | Werkwijze voor het bereiden van farmacologisch actieve verbindingen. |
-
1979
- 1979-10-25 GB GB7937081A patent/GB2035313B/en not_active Expired
- 1979-10-25 CH CH960479A patent/CH645098A5/de not_active IP Right Cessation
- 1979-10-29 IT IT69110/79A patent/IT1192784B/it active
- 1979-10-31 AT AT0702779A patent/AT368991B/de not_active IP Right Cessation
- 1979-11-02 DE DE19792944257 patent/DE2944257A1/de not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7510344A (nl) * | 1974-09-02 | 1976-03-04 | Smith Kline French Lab | Werkwijze voor het bereiden van farmacologisch actieve verbindingen. |
Non-Patent Citations (1)
| Title |
|---|
| C.A. 91, 175354 z * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2528833A1 (fr) * | 1982-06-16 | 1983-12-23 | May & Baker Ltd | Derives de la cystamine, leur preparation et les compositions comme facteur de croissance qui les contiennent |
Also Published As
| Publication number | Publication date |
|---|---|
| AT368991B (de) | 1982-11-25 |
| GB2035313A (en) | 1980-06-18 |
| CH645098A5 (de) | 1984-09-14 |
| IT1192784B (it) | 1988-05-04 |
| IT7969110A0 (it) | 1979-10-29 |
| GB2035313B (en) | 1983-01-06 |
| ATA702779A (de) | 1982-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1620694C3 (de) | Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren | |
| DE1543181A1 (de) | -phenylessigsaeuren und Verfahren zu deren Herstellung | |
| DE2944257A1 (de) | Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl) guanidin | |
| EP0040346B1 (de) | Verfahren zur Raffination des rohen Kondensationsproduktes aus Aminoalkylalkanolaminen und Fettsäuren sowie gewünschtenfalls zur anschliessenden Gewinnung von Amphotensiden mit erhöhter Lagerstabilität | |
| DE1958514A1 (de) | Verfahren zur Herstellung von Apovincaminsaeureamiden | |
| DE3538746C2 (it) | ||
| DE2011078A1 (de) | Verfahren zur Herstellung von reinem Hexetidin | |
| EP0109495B1 (de) | Verfahren zur Herstellung von beta-Hydroxy-alpha-aminocarbonsäuren | |
| DE1814334C3 (it) | ||
| DE2065698B2 (de) | Verfahren zur Herstellung von 2-Isopropyl-6-methyl-4(3H)-pyrimidon | |
| DE525185C (de) | Verfahren zur Darstellung von Magnesiumcyanid | |
| AT206876B (de) | Verfahren zur Herstellung von neuen Alkinylsulfonsäuren | |
| DE954417C (de) | Verfahren zur Herstellung von ª‡-Amino-ª‰-mercaptocarbonsaeuren | |
| DE2112778B2 (de) | Verfahren zur Herstellung von 2-CyBn-S^Ae-IeITaChIOr- bzw. brombenzoesäurealkylestern | |
| DE2350395C3 (de) | N-(m-Trifluormethylthiophenyl)-piperazin, deren Salze, Verfahren zu deren Herstellung und deren Verwendung als Zwischenverbindung zur Herstellung von Piperazin-Derivaten | |
| DE1024954B (de) | Verfahren zur Herstellung von N-disubstituierten Dithiocarbaminsaeureestern, die im Alkoholrest Sulfonsaeuregruppen enthalten | |
| AT207373B (de) | Verfahren zur Herstellung von Äthyleniminderivaten | |
| DE1518011C (de) | (4-Chlor-2-methylphenoxy)-(4-chlorphenyl)-essigsäure und deren pharmakologisch verträglichen Salze sowie Verfahren zu deren Herstellung | |
| DE2714255A1 (de) | Verfahren zur herstellung von m-aminophenolen und deren verwendung | |
| DE1236524C2 (de) | Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin | |
| DE3317159C2 (it) | ||
| DE2606855C2 (de) | Verfahren zur Herstellung von Propionsäure-3,4-dichloranilid | |
| DE1518230C (de) | Verfahren zur Herstellung von N Benzyl N", N" dimethylguamdin | |
| DE818049C (de) | Verfahren zur Herstellung von schwefelhaltigen Diazoaminoverbindungen | |
| DE805523C (de) | Verfahren zur Herstellung von Histaminen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS |
|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |