Pyridine → 4-nitro-N-[2-(trifluoromethyl)phenyl]benzenesulfonamide

Participants

Reaction Steps

A solution of 2-(trifluoromethyl)aniline (1.51 g, 9.37 mmol) and pyridine (1.08 mL, 13.38 mmol) in DCM (30 mL) was treated with 4-nitrobenzenesulfonyl chloride (1.48 g, 6.69 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 M aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Trituration with pentane gave 4-nitro-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (1.91 g, 82%). 1H NMR (300 MHz, CDCl3) δ 8.31-8.23 (m, 2H), 7.95-7.85 (m, 3H), 7.64-7.50 (m, 2H), 7.31 (t, J=7.7 Hz, 1H), 6.89 (br s, 1H). LCMS (m/z, Method A) ES+ 347.1 [M+1]+.

Provenance & Evidence