4-Toluenesulfonyl chloride → N-(6-chloropyridazin-3-yl)-4-methylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

6-Chloro-pyridazin-3-ylamine (7 g, 54 mmol) was taken up in pyridine (54 mL) and TsCl (11.34 g, 59 mmol) was added. The solution was heated at 80-90° C. for 24 h. The solution was concentrated and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine (2×50 mL), dried over sodium sulfate and concentrated. Purification by silica gel chromatography (ethyl acetate/hexane) afforded the title compound (4 g, 26%). 1H NMR (DMSO-d6, 300 MHz): δ 2.4 (s, 3H), 7.4 (d, 3H), 7.54 (d, 1H), 7.8 (m, 3H), 12.5 (br, 1H)

Provenance & Evidence