Reactions of monoprotic thioureas with ethyl α-chloroacetoacetate, ethyl bromomalonate, and ethyl bromocyanoacetate
Abstract
N,N,-Dialkyl-N′-arylthioureas (1) with ethyl α-chloroacetoacetate, furnished dialkylamine hydrochlorides, aryl isothiocyanates, 2-arylimino-1,3-oxathioles (2), 2-arylimino-3-aryl-Δ4-thiazolines (3), diarylthioureas (9), and carbonyl sulphide. With ethyl bromomalonate the products were dialkylamine hydrobromides, aryl isothiocyanates, 2-arylimino-3-arylthiazolidin-4-ones (11), and diarylthioureas (9). Ethyl bromocyanoacetate gave an ethyl cyano{[dimethylamino(phenylimino)methyl]thio}acetate (13). Compound (13) with triethylamine gave the starting thiourea (1) and diethyl dicyanofumarate.