4-Toluenesulfonyl chloride → HCID 178427411, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromopyridin-2-amine (10.4 g, 60 mmol, Aldrich, St. Louis, Mo.) in pyridine (50 mL) was added p-toluenesulfonyl chloride (13 g, 66 mmol). The mixture was heated to 85° C. for 12 h. The solvent was removed under reduced pressure and the residue was taken up in 1 L of water and stirred for 1.5 h. The solid was collected by filtration and recrystallized from EtOAc to afford N-(5-bromopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (11.3 g, 57% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.23 (s, 1H), 8.27 (d, J=2.5 Hz, 1H), 7.89 (dd, J=8.8 Hz, 2.4 Hz, 1H), 7.79 (d, J=8.2 Hz, 2H), 7.37 (d, J=8.2 Hz, 2H), 7.03 (d, J=8.8 Hz, 1H), 2.35 (s, 3H).

Provenance & Evidence