O-Xylene → 2-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

Participants

Reaction Conditions

Reaction Steps

N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea (2.94 g) and zinc chloride (6.08 g) were added to xylene (50 ml) at room temperature, and the mixture was heated to 90° C. and stirred at the same temperature for 1.5 hour. After cooling, water was added to the reaction mixture, which was neutralized by addition of potassium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water. The solvent was removed by distillation under reduced pressure, and the residual oil was subjected to preparative liquid chromatography, which afforded 1.92 g of 2-imino-3-(3-(trifluoromethyl)phenyl)-5-methylidenethiazolidine (74% yield). From the results of analysis by liquid chromatography, the purity was determined to be not lower than 99%.

Provenance & Evidence