Pyridine → HCID 22663775, compound

Participants

Reaction Steps

To a solution of 2-chloro-N-methylaniline (4.96 mmol, 1.1 eq., 702 mg) and pyridine (5.86 mmol, 464 mg) in 20 mL of methylene chloride was added 3-nitrobenzenesulfonyl chloride (4.51 mmol, 1.0 g) in one portion. The reaction mixture was stirred 16 hr and diluted with methylene chloride and water. The aqueous layer was separated and extracted once with methylene chloride. The combined organic layers were extracted once with a saturated solution of aqueous sodium carbonate, once with water, and then dried over sodium sulfate. The crude product was purified using flash chromatography (10-60% ethyl acetate/hexane) to give N-(2-chlorophenyl)-N-methyl-(3-nitrophenyl)sulfonamide which solidifies on standing. 1H NMR (300 MHz) 3.29 (s, 3H), 7.25-7.45 (m, 4H), 7.71 (t, J=7.82 Hz, 1H), 8.06 (d, J=7.82 Hz, 1H), 8.40-8.50 (m, 1H), 8.60-8.65 (m, 1H). MS (ESI): m/e 327.13, 329.13 (M+1).

Provenance & Evidence