Water → Pyridine-2-sulfonyl Chloride

Participants

Reaction Conditions

Reaction Steps

2-Mercaptopyridine (126 mg, 1 mmol) was dissolved in 5 mL of concentrated sulfuric acid to form a yellow solution, which was cooled to around −15° C. with a sodium chloride/ice (1/3) bath. Aqueous sodium hypochlorite solution (10-15%, 11 mL, 15-20 mmol) was added to the solution slowly enough to maintain the internal temperature of the reaction mixture below 10° C., with vigorous stirring. The reaction mixture was stirred at 0° C. for 1 hour and then 10 mL of water was added, which was then extracted with methylene chloride (20 mL×3). The combined organic phase was washed with water, dried with anhydrous magnesium sulfate, and then concentrated in vacuo. Pyridine-2-sulfonyl chloride (145 mg, 72%) was produced as a yellowish viscous liquid. 1H NMR (CDCl3): δ 7.684-7.729 (m, 1H), 8.043-8.143 (m, 2H), 8.84 (d, J=4.10 Hz, 1H).

Provenance & Evidence