Potassium Carbonate → N-(2-Hydroxyethyl)-2-(2,4,6-trichlorophenylamino)-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-Amino-N-(2-hydroxyethyl)-benzene sulfonamide (160 mg, 0.74 mmol), 1,3,5-trichloro-2-bromobenzene (241 mg, 0.93 mmol), K2CO3 (256 mg, 1.85 mmol) and xantphos (43 mg, 0.074 mmol) in acetonitrile (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (34 mg, 0.037 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 160° C. for 120 minutes. The reaction was cooled before filtering through celite. The crude reaction mixture was part-purified by column chromatography eluting with ethyl acetate:hexane and the concentrated fractions further purified by preparative chromatography under acidic conditions to afford the named product (49.0 mg, 17%); δH (400 MHz, DMSO) 7.83 (3H, m), 7.75+7.45 (1H, d), 7.59+7.10 (1H, s), 7.55+7.38 (1H, t), 7.16+6.95 (1H, t), 7.10+6.40 (1H, d), 4.73 (1H, m), 3.35 (2H, m) and 2.83 (2H, m); LCMS Rt=7.92 min, m/z (ES+) 397 (M+H).

Provenance & Evidence