2(3H)-Benzoxazolone → 6-Benzoxazolesulfonyl chloride, 2,3-dihydro-2-oxo-

Participants

Reaction Conditions

Reaction Steps

Sulfurochloridic acid (70 g, 603.45 mmol) was cooled to 0° C. and benzo[d]oxazol-2(3H)-one (1.8 g, 13.33 mmol) was added in several batches, maintaining the temperature at about 0° C. The resulting solution was stirred at room temperature for 3 hours, then quenched by the addition 400 mL of iced water. The resulting solution was extracted with ethyl acetate (3×100 mL) and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:10 ethyl acetate/petroleum ether solvent system to afford 0.8 g (26%) of 2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride as a white solid. 1H NMR (CDCl3) δ 8.26 (s, 1H), 8.00 (d, 1H), 7.98 (d, 1H), 7.32 (s, 1H).

Provenance & Evidence