JPS6452760A - Production of imidazole derivative - Google Patents
Production of imidazole derivativeInfo
- Publication number
- JPS6452760A JPS6452760A JP62209381A JP20938187A JPS6452760A JP S6452760 A JPS6452760 A JP S6452760A JP 62209381 A JP62209381 A JP 62209381A JP 20938187 A JP20938187 A JP 20938187A JP S6452760 A JPS6452760 A JP S6452760A
- Authority
- JP
- Japan
- Prior art keywords
- aminoethyl
- methyl
- dithiocarbonate
- hydroxymethylimidazole
- cimetidine
- 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.)
- Granted
Links
- 150000002460 imidazoles Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical compound CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 abstract 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 abstract 2
- 229960001380 cimetidine Drugs 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 abstract 1
- HPOWDPHMQMGGNW-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylazanium;chloride Chemical compound Cl.CC=1N=CNC=1CSCCN HPOWDPHMQMGGNW-UHFFFAOYSA-N 0.000 abstract 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 abstract 1
- 102000003710 Histamine H2 Receptors Human genes 0.000 abstract 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
Abstract
PURPOSE:To obtain the titled compound useful as an intermediate for cimetidine at a low cost, by reacting 4-methyl-5-hydroxymethylimidazole with S,S'-bis(2- aminoethyl)dithiocarbonate as raw materials in acidic solvent. CONSTITUTION:Readily synthesized 4-methyl-5-hydroxymethylimidazole is reacted with S,S'-bis(2-aminoethyl)dithiocarbonate expressed by formula II which can be readily synthesized by reacting 2-mercaptothiazoline and chloroethylamine in an acidic solvent, such as hydrochloric acid or acetic acid, in >=5wt.% concentration at 70 deg.C - refluxing temperature for 5-30hr to vacuum concentrate the resultant reaction solution and separate the aimed compound, such as 4- methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole hydrochloride, expressed by formula III and useful as a synthetic intermediate for cimetidine which is an antiulcer agent having inhibitory action on histamine H2 receptor, etc., as a solid substance. The resultant substance is then recrystallized from a alcohols to afford the aimed compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62209381A JP2585283B2 (en) | 1987-08-25 | 1987-08-25 | Method for producing imidazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62209381A JP2585283B2 (en) | 1987-08-25 | 1987-08-25 | Method for producing imidazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6452760A true JPS6452760A (en) | 1989-02-28 |
| JP2585283B2 JP2585283B2 (en) | 1997-02-26 |
Family
ID=16571972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62209381A Expired - Lifetime JP2585283B2 (en) | 1987-08-25 | 1987-08-25 | Method for producing imidazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2585283B2 (en) |
-
1987
- 1987-08-25 JP JP62209381A patent/JP2585283B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2585283B2 (en) | 1997-02-26 |
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