Sodium hydride → HCID 178491032, compound

Participants

Reaction Steps

To a mixture of 2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenol (0.110 g, 0.45 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (0.020 g of a 60% w/w dispersion in mineral oil, 0.50 mmol) and the reaction mixture was stirred for 1 h at ambient temperature. N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.210 g, 0.47 mmol) was added and the reaction mixture was stirred for 16 h at ambient temperature. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (10 mL). The organic phase was washed with water (2 10 mL) and brine (2 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient of ethyl acetate in hexanes to afford 4-(2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as an off-white solid in 34% yield (0.102 g): MS (ES+) m/z 669.7 (M+1), 671.7 (M+1).

Provenance & Evidence