Hydrochloric Acid → 3-Cyanobenzene-1-sulfonyl chloride

Participants

Reaction Steps

3-Aminobenzonitrile (2.5 g, 21 mmol) was dissolved in conc. HCl (20 mL) and water (20 mL), cooled to 0° C. and a solution of sodium nitrite (1.5 g, 22 mmol) in water (5 mL) was added dropwise. The reaction mixture was stirred for 10 min to complete the diazonium salt formation. In a separate flask was added copper(I) chloride (0.2 g) over a saturated solution of sulfur dioxide in AcOH (25 mL) and stirred at 0° C. for 10 min. The resulting solution was added dropwise to the diazonium salt and stirred at 0° C. for 1 h. The reaction mixture poured into ice water and the product was extracted with tert-butylmethylether. The combined organic layer was washed with water and brine. The crude product was purified by column chromatography (silica gel 60-120 mesh using 5% EtOAc in petroleum ether) to get the pure 3-cyanobenzene-1-sulfonyl chloride (1.9 g, yield 45%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.35 (t, J=1.5 Hz, 1H), 8.31-8.27 (m, 1H), 8.06-8.02 (m, 1H), 7.82 (t, J=7.9 Hz, 1H).

Provenance & Evidence