Synthesis and rearrangements in the thiazoline imine series

Abstract

The rection of 1-acyl-3-(p-ethoxyphenyl)thioureas with chloroacetone or α-bromoacetophenone has given 2-acylimino-3-(pethoxy-phenyl)-4-hydroxy-4-methylthiazolidines or the corresponding 4-phenyl compounds, which readily split out water and are converted into the corresponding acylated 4-thiazolines. The action of aqueous alcoholic hydrochloric acid leads to hydrolysis with the formation of the corresponding 2-imino-3-p-ethoxyphenylthiazolines. When the latter are boiled with 20% hydrochloric acid, they undergo rearrangement to 2-p-ethoxyphenylaminothiazoles.