JPS57130975A - Preparation of imidazole derivative - Google Patents
Preparation of imidazole derivativeInfo
- Publication number
- JPS57130975A JPS57130975A JP56016345A JP1634581A JPS57130975A JP S57130975 A JPS57130975 A JP S57130975A JP 56016345 A JP56016345 A JP 56016345A JP 1634581 A JP1634581 A JP 1634581A JP S57130975 A JPS57130975 A JP S57130975A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- formula
- mercaptomethylimidazole
- chloroethanol
- toluenesulfonate
- 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.)
- Pending
Links
- 150000002460 imidazoles Chemical class 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- GCYDEHNKSNMNMN-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol Chemical compound CC=1NC=NC=1CS GCYDEHNKSNMNMN-UHFFFAOYSA-N 0.000 abstract 2
- ZXNMIUJDTOMBPV-UHFFFAOYSA-N 2-chloroethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCl)C=C1 ZXNMIUJDTOMBPV-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- SIQWQBQGWREFSE-UHFFFAOYSA-N 1-cyano-2-methylguanidine Chemical compound CNC(N)=NC#N SIQWQBQGWREFSE-UHFFFAOYSA-N 0.000 abstract 1
- IPVYMXZYXFFDGW-UHFFFAOYSA-N 1-methylpiperidin-4-ol;hydrochloride Chemical compound Cl.CN1CCC(O)CC1 IPVYMXZYXFFDGW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 abstract 1
- 229960001380 cimetidine Drugs 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229960001340 histamine Drugs 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Abstract
PURPOSE: To prepare the titled substance useful as an intermediate for the synthesis of pharmaceuticals, in high yield, in one step, by using 4-methyl-5-mercaptomethylimidazole available at a low cost as a starting raw material, and reacting with 2-chloroethanol p-toluenesulfonate.
CONSTITUTION: 4-Methyl-5-mercaptomethylimidazole of for mulaIor its hydrocholoride is made to react with 2-chloroethanol p-toluenesulfonate of formula II in the presence of an alkali such as NaOH, at or below room temperature, pref. about 30W0°C in a solvent such as ethanol to obtain the titled compound of formula III. The compound of formula III can be converted to cimetidine which is a medicine having histamine H2 receptor blocking effect, by reacting with N-methyl-N'-cyano-guanidine of formula IV in a solvent in the presence of an alkali metal condensation agent under heat refluxing.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56016345A JPS57130975A (en) | 1981-02-06 | 1981-02-06 | Preparation of imidazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56016345A JPS57130975A (en) | 1981-02-06 | 1981-02-06 | Preparation of imidazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS57130975A true JPS57130975A (en) | 1982-08-13 |
Family
ID=11913791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56016345A Pending JPS57130975A (en) | 1981-02-06 | 1981-02-06 | Preparation of imidazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57130975A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51101976A (en) * | 1975-02-03 | 1976-09-08 | Smith Kline French Lab |
-
1981
- 1981-02-06 JP JP56016345A patent/JPS57130975A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51101976A (en) * | 1975-02-03 | 1976-09-08 | Smith Kline French Lab |
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