4-Chlorobenzenesulfonyl chloride → HCID 66973638, compound

Participants

Reaction Steps

To a suspension of 4-chloro-N-(5-fluoro-2-oxo-1,2-dihydropyrimid-4-yl)benzamide (0.10 g, 0.37 mmol) in CH2Cl2 (4 mL) were added Et3N (0.08 g, 0.82 mmol) and 4-chlorobenzenesulfonyl chloride (0.087 g, 0.41 mmol) at 0° C., and the resulting mixture was warmed to room temperature and stirred for 3 h. The reaction was diluted with CH2Cl2 (10 mL) and washed with brine. The phases were separated and the organic phase was dried over sodium sulfate (Na2SO4), filtered, and concentrated to an amber oil (0.295 g). Purification by normal phase chromatography (12 g SiO2; gradient, 0 to 35% EtOAc/hexanes) afforded 4-chloro-N-[1-(4-chlorobenzenesulfonyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide (0.025 g, 26%) as a white solid: mp 169-172° C.; 1H NMR (300 MHz, CDCl3) δ 12.59 (s, 1H), 8.29-8.15 (m, 3H), 8.05 (d, J=8.8 Hz, 2H), 7.59 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.6 Hz, 2H); ESIMS m/z 442 ([M+H]+), 440 ([M−H]−).

Provenance & Evidence