Dimethylformamide → 4-Chloro-3-methyl-2-oxo-2,3-dihydro-1,3-thiazole-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

At 0° C., N,N-dimethylformamide (2 mL, 27 mmol) was added to a solution of 3-methyl-thiazolidine-2,4-dione (33a) (1.77 g, 13.5 mmol) in phosphorus oxychloride (3.77 mL, 40.5 mmol). The reaction mixture was stirred at 110° C. for 3 hours, cooled to room temperature and quenched with a mixture of ice and ethyl acetate. The organic layer was washed with water (30 mL), brine (30 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure to give the desired aldehyde (33b) as a yellow solid (1.9 g, 10.7 mmol, 79%).

Provenance & Evidence