Dimethylamine → 1-Methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea hydrochloride

Participants

Reaction Steps

A suspension of 1-methoxycarbonyl-3-(2-chloroacetamidophenyl)thiourea (1.51 g) in benzene (50 ml) was treated with a solution of dimethylamine in benzene (15 ml., 10% w/w). The mixture was heated to reflux for 15 minutes with stirring. A further quantity of dimethylamine in benzene (5ml, 10% w/w) was added, and the mixture heated to reflux for a further 15 minutes with stirring. The mixture was allowed to stand for 1 hour, during which time it cooled to room temperature, and was then filtered. The filtrate was treated with an excess of a saturated solution of hydrogen chloride in diethyl ether. The precipitate was filtered off, treated with water (20 ml), some insoluble solid was filtered off, and the aqueous filtrate neutralised by treatment with 2N aqueous sodium hydroxide solution. The resultant solid was filtered off, dissolved in the minimum quantity of ethanol and the solution treated with diethyl ether, followed by an excess of a saturated solution of hydrogen chloride in diethyl ether. The resultant solid was filtered off and recrystallised from ethanol to give 1-methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea hydrochloride (0.25 g), m.p. 187°-188° C. (with decomposition).

Provenance & Evidence