2,6-Dichloroaniline → N-(2,6-Dichlorophenyl)-4,6-dimethyl-2-pyrimidinesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichloroaniline (1.0 g, 6.2 mmol) in dimethoxyethane (25 mL) was added butyl lithium (3.9 mL, 6.24 mmol). After 15 minutes, the solution was cooled to -30° and 4,6-dimethyl-2-pyrimidinesulfonyl fluoride (1.18 g, 6.2 mmol) was added. The mixture stirred for 12 hours with warming to 25° C. The mixture was concentrated and the residue was treated with 1N NaOH (2 mL) and extracted with ethyl acetate. The aqueous layer was acidified with 1N HCl and a solid was collected, m.p. 261°-263° C. NMR (90 MHZ) D6 -Acetone: δ 7.5 (m, 4H) and 2.5 (s, 6H).

Provenance & Evidence