Chlorosuccinimide → N-(4,5-Dichloropyridin-2-yl)pivalamide

Participants

Reaction Steps

NCS (3.14 g. 23.5 mmol) was added to a solution of N-(4-chloropyridin-2-yl)pivalamide (1.00 g, 4.7 mmol) in dry acetonitrile (10 mL). The resulting suspension was heated for 3 h and then cooled to r.t. The solvent was removed in vacuo and the crude mixture was diluted with ethyl acetate (50 mL). The organic phase was washed with aqueous NaOH (10%, 2×20 mL), water (20 mL) and dried (MgSO4). The solvent was removed in vacuo and the crude mixture was purified by flash chromatography on silica, eluting with ethyl acetate and hexane (1/9), to give the title compound as a colourless solid (0.87 g, 75%).

Provenance & Evidence