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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 330099Generated: October 30, 2026

Formamide → HCID 178484997, compound

https://huagongshe.com/reaction/330099

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormamideHCID 713—
ReactantAmmonium formateHCID 2723923—
ReactantN-cyano-N'-[2-(2-formyloxy-3-oxobutylthio)ethyl]-N"-methylguanidineHCID 14622764—
ReactantMethylorthoformateHCID 53629101—
ProductHCID 178484997HCID 17848499756%

Reaction Conditions

Temperature100 °C

Reaction Steps

136 mg of N-{2-(2-formyloxy-3-oxobutylthio)ethyl}-N'-cyano-N"-methylguanidine and 530 mg of methyl orthoformate were dissolved in 2.5 m; of formamide, and 320 mg of ammonium formate was added. The mixture was stirred at 100° C. for 2 hours. Formamide was evaporated from the reaction mixture under reduced pressure. The residue was chromatographed on a column of silica gel (eluent: chloroform/methanol=4/1), and then recrystallized from isopropanol to give 71 mg (yield 56%) of the desired product (Cimetidine) as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04894475
Source datasetuspto-grants-1990_01
ORD IDord-b225c7d67cd84417b6419f7f2d2468fc
Source noteuspto-grants-1990_01