2-Chloro-6-methylaniline → N-(2-Chloro-6-methylphenyl)-4,6-dimethylpyrimidine-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6-methylaniline (0.5 g, 3.5 mmol) in dimethoxyethane (15 mL) cooled to 0° C. was added butyl lithium (2.2 mL, 3.5 mmol) and the mixture was allowed to stir for 15 minutes. Then 4,6-dimethyl-2-pyrimidinesulfonyl fluoride (0.66 g, 3.5 mmol), prepared according to Brown and Hoskins, J. Chem. Soc. Perkin 1, 522-527 (1972) was added. The mixture stirred with warming to 25° C. for 1 hour. The mixture was concentrated and the residue triturated with butyl chloride. The resultant solid was acidified with 1N HCl and the solid was filtered. The product was a yellow-brown solid, m.p. 215°-219° C. NMR (200 MHZ) D6 -Acetone: δ 8.2 (bs, 1H), 7.4 (s, 1H), 7.2 (bs, 3H), 2.5 (s, 6H) and 2.35 (s, 3H).

Provenance & Evidence