Dimethylformamide → N-benzyl-2-formyl-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

To a solution of N-benzyl-4-methylthiazole-5-carboxamide (1.00 g, 4.31 mmol) in tetrahydrofuran (20 mL) was added lithium bis(trimethylsilyl)amide (9.5 mL of 1.0 M solution in tetrahydrofuran, 9.5 mmol) at −78° C. The reaction mixture was stirred for 5 minutes, and N,N-dimethylformamide (0.35 mL, 4.54 mmol) was added. The reaction mixture was slowly warmed to ambient temperature over 4 hours, quenched with 5% hydrochloric acid (10 mL), extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound in 98% yield (1.1 g): MS (ES+) m/z 261.1 (M+1).

Provenance & Evidence