3-(Trifluoromethyl)benzaldehyde → 3-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-5-[[3-(trifluoromethyl)phenyl]methylene]-4-thiazolidinone

Participants

Reaction Steps

A slurry of 3-[(1,3-benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone (see example 37), m-trifluoromethylbenzaldehyde (10 ml, excess) and acetic acid/piperidine (1 ml) in 250 ml of anhydrous glyme is heated at reflux for 7 days. The reaction mixture is concentrated in vacuo and the oily residue extracted with hexane. The solid thus obtained is slurried in 1000 ml of dichloromethane and stirred at room temperature overnight. The slurry is filtered and the filtrate concentrated in vacuo. The solid residue thus obtained is recrystallized from dimethylformamide to yield 500 mg of the title compound, melting point 268°-269° C.

Provenance & Evidence