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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 477286Generated: October 29, 2026

Formamide → HCID 178484998, compound

https://huagongshe.com/reaction/477286

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormamideHCID 713—
ReactantAmmonium formateHCID 2723923—
ReactantN-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidineHCID 14457222—
ReactantMethylorthoformateHCID 53629101—
ReactantAmmonium sodium phosphate tetrahydrateHCID 56924540—
ProductHCID 178484998HCID 17848499887%

Reaction Conditions

Temperature100 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04886910
Source datasetuspto-grants-1989_12
ORD IDord-d8c756f6edd649dda9bd58fd304200f5
Source noteuspto-grants-1989_12