Hydrochloric Acid → 1-Methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea

Participants

Reaction Steps

A suspension of N-(2-aminophenyl)-2-dimethylaminoacetamide (4.8 g) in dry acetonitrile (20 ml) was stirred vigorously during the dropwise addition of methoxycarbonyl isothiocyanate (3.5 g), the temperature being maintained between 15° C. and 20° C. by external cooling, and afterwards for a further 5 minutes. The mixture was then diluted with diethyl ether (500 ml) and treated with an excess of a saturated solution of hydrogen chloride in diethyl ether. The precipitate was filtered off, dissolved in the minimum quantity of water, and treated with an excess of a 2N aqueous solution of sodium hydroxide. The precipitate was filtered off and recrystallised twice from benzene to give 1-methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea (3.5 g), m.p. 130°-131° C. (with decomposition).

Provenance & Evidence