Acetyl chloride → HCID 22287249, compound

Participants

Reaction Conditions

Reaction Steps

N-[2-Chloro-4-(4-aminophenylsulphanyl)phenyl]-2-acetoxy-2-methylpropanamide (Method 22) (0.50 g) was dissolved in DCM (10 ml) and cooled to 0-5° C. in an ice bath. Triethylamine (0.46 ml) was added followed by dropwise addition of acetyl chloride (0.1 ml) and the mixture was allowed to warm to ambient temperature over 2 hours. Ethyl acetate (20 ml) was added and the solution was washed with water (2×10 ml) and brine then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography eluting with 40-80% ethyl acetate/hexane to give the title compound (0.470 g) as a solid. NMR (CDCl3): 1.8 (s, 6H), 2.2 (d, 6H), 7.2-7.3 (m, 5H), 7.5 (d, 2H), 8.3 (d, 1H), 8.4 (s, 1H); MS (ESP−): 419; EA: found: C, 56.7; H, 5.0; N, 6.0%; C20H21ClN2O4S.0.4 EtOAc requires C, 56.9; H, 5.3; N, 6.1%.

Provenance & Evidence