2-(Dimethylamino)acetyl chloride hydrochloride → 4-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzene

Participants

Reaction Steps

A stirred solution of 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene (8.35 g) in dry dimethylformamide (60 ml) was treated at room temperature with N,N-dimethylglycyl chloride hydrochloride (5.53 g). The mixture was heated to 40°-50° C for 45 minutes, then cooled, and diluted with diethyl ether (900 ml). An oil precipitated which crystallised on standing. This solid was filtered off, washed with diethyl ether (100 ml), and suspended in a mixture of chloroform (100 ml) and water (100 ml). Sodium carbonate (3.5 g) was added and the mixture was stirred for 20 minutes. The chloroform layer was separated and the aqueous layer was extracted twice with chloroform (2 × 50 ml). The organic layers were combined, dried over magnesium sulphate and evaporated to dryness. The residual solid was recrystallised from isopropanol to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzene (8.5 g), m.p. 142° C (with decomposition).

Provenance & Evidence