Dimethylformamide → 2-Acetylthiomethylthiopyridine

Participants

Reaction Steps

To a solution of 2-mercaptopyridine (1.11 g : 9.98 mMol.) in dimethylformamide (10 ml) is added sodium hydride (400 mg : 60% dispersion in oil), and the mixture is stirred at room temperature for 2 to 3 minutes. To this reaction mixture at -30° C. is added a solution of chloromethyl thiolacetate (1.12 g : 9.00 mMol.) in dimethylformamide (2 ml), and the mixture is stirred at -20 to -30° C. for 1 hour. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1) to give 2-acetylthiomethylthiopyridine (1.43 g) as yellow oil. Yield: 72%.

Provenance & Evidence