Hydrochloric Acid → 1-Ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea hydrochloride

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Reaction Steps

Ethoxycarbonyl isothiocyanate (5.6 g) was added dropwise, with cooling to maintain the temperature between 15° and 20° C., to a vigorously stirred solution of N-(2-amino-4-methoxycarbonylaminophenyl)-2-dimethylaminoacetamide (10.75 g) in dry acetone (200 ml). The resulting mixture was stirred for a further 30 minutes and then poured into an excess of water. The precipitated solid was filtered off to give crude 1-ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea, m.p. 171°-172° C, which was then dissolved in the minimum of ethanol. Diethyl ether (300 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 methanol/ethanol to give 1-ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea hydrochloride (7.5 g), m.p. 211°-213° C. (with decomposition).

Provenance & Evidence