Hydrochloric Acid → 1-Ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea hydrochloride

Participants

Reaction Steps

Petroleum spirit (b.p. 60°-80° C; 50 ml) was added to a solution of N-(2-amino-4-n-butylphenyl)-2-dimethylaminoacetamide (4.98 g) in benzene (50 ml) and the solution stirred vigorously while ethoxycarbonyl isothiocyanate (2.65 g) was added dropwise, with external cooling, to maintain the temperature between 15° C. and 20° C. After ten minutes, the precipitated solid was filtered off and recrystallised from benzene to give crude 1-ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea, m.p.152°-155° C. (with decomposition), which was then dissolved in the minimum of ethanol. Diethyl ether (200 ml) was added, followed by an excess of a saturated solution of hydrogen chloride in diethyl ether. The precipitated solid was filtered off and recrystallised from ethanol/ethyl acetate to give 1-ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea hydrochloride (1.9 g), m.p. 174°-176° C. (with decomposition).

Provenance & Evidence