Ethanol → 2-amino-4-[N-4-chlorophenyl-N-isopropyl (carbamoylethylidene)] thiazole

Participants

Reaction Steps

A solution containing 43.3 g (0.13 mole) of N-isopropyl-4'-chloro-4-bromo-2-methylacetoacetanilide, 10.2 g (0.14 mole) of thiourea and 300 ml of ethanol was refluxed for two hours. A portion of the ethanol was evaporated and water was added. The reaction solution was made basic with ammonium hydroxide. After drying, the white solid weighed 33 g (78%), M.P. 145°-47°. N.M.R. (dimethyl-d6 sulfoxide, CDCl3) ∂0.9-1.3 (CH3, 9 protons), 3.1-3.4 (CH), 4.6-5.1 (CH, isopropyl), 5.9 (hetero-aromatic), 6.5 (NH2), 7.0-7.5 (aromatic).

Provenance & Evidence