Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formamide | HCID 713 | — |
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidine | HCID 14457222 | — |
| Reactant | Methylorthoformate | HCID 53629101 | — |
| Reactant | Ammonium sodium phosphate tetrahydrate | HCID 56924540 | — |
| Product | HCID 178484998 | HCID 178484998 | 87% |
Reaction Steps
To 136 mg of N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidine, 320 mg of amonium formate, 0.6 ml of methyl orthoformate and 209 mg of sodium ammonium hydrogenphosphate tetrahydrate was added 2.5 ml of formamide, and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled and insoluble substances were removed, and the solvent was removed under reduced pressure and the obtained residue was refined by silica gel column chromatography (eluting solvent: chloroform/ethanol=5/1) and recrystallized from isopropanol/ether (60/40) to obtain 100 mg of intended Cimetidine (the yield was 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04886910 |
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| Source dataset | uspto-grants-1989_12 |
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| ORD ID | ord-d8c756f6edd649dda9bd58fd304200f5 |
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| Source note | uspto-grants-1989_12 |
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