JPS6121632B2 - - Google Patents
Info
- Publication number
- JPS6121632B2 JPS6121632B2 JP57234649A JP23464982A JPS6121632B2 JP S6121632 B2 JPS6121632 B2 JP S6121632B2 JP 57234649 A JP57234649 A JP 57234649A JP 23464982 A JP23464982 A JP 23464982A JP S6121632 B2 JPS6121632 B2 JP S6121632B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- cyano
- guanidine
- reaction
- mixture
- 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
- -1 4-methyl-5-imidazolyl Chemical group 0.000 claims description 8
- GCYDEHNKSNMNMN-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol Chemical compound CC=1NC=NC=1CS GCYDEHNKSNMNMN-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- SIQWQBQGWREFSE-UHFFFAOYSA-N 1-cyano-2-methylguanidine Chemical class CNC(N)=NC#N SIQWQBQGWREFSE-UHFFFAOYSA-N 0.000 claims description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229960001380 cimetidine Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- GAIOTNZPXCFNJU-UHFFFAOYSA-N 1-(2-chloroethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCCl GAIOTNZPXCFNJU-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000005035 acylthio group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- AAYWCPDQGWTFOV-UHFFFAOYSA-N s-[(5-methyl-1h-imidazol-4-yl)methyl] ethanethioate Chemical compound CC(=O)SCC=1N=CNC=1C AAYWCPDQGWTFOV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FNMHARGLJLWHAA-UHFFFAOYSA-N 1-(2-bromoethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCBr FNMHARGLJLWHAA-UHFFFAOYSA-N 0.000 description 1
- KWULCRGWFZACSD-UHFFFAOYSA-N 2-(2-chloroethyl)guanidine Chemical compound NC(N)=NCCCl KWULCRGWFZACSD-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- OFFPEAOWWDXZOY-UHFFFAOYSA-N 2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CN=C(N)NCCSCC=1N=CNC=1C OFFPEAOWWDXZOY-UHFFFAOYSA-N 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57234649A JPS59122475A (ja) | 1982-12-27 | 1982-12-27 | イミダゾ−ル系化合物の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57234649A JPS59122475A (ja) | 1982-12-27 | 1982-12-27 | イミダゾ−ル系化合物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59122475A JPS59122475A (ja) | 1984-07-14 |
| JPS6121632B2 true JPS6121632B2 (enrdf_load_stackoverflow) | 1986-05-28 |
Family
ID=16974326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57234649A Granted JPS59122475A (ja) | 1982-12-27 | 1982-12-27 | イミダゾ−ル系化合物の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59122475A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113234018B (zh) * | 2021-05-11 | 2022-08-23 | 石家庄市普力制药有限公司 | 一种西咪替丁的生产方法 |
-
1982
- 1982-12-27 JP JP57234649A patent/JPS59122475A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59122475A (ja) | 1984-07-14 |
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