Sodium hydride → HCID 11208041, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.10 g, 60% dispersion in mineral oil) was added at ambient temperature under nitrogen in small portions to a stirred solution of 2-acetylamino-5-chloro-benzenesulfinic acid (0.55 g) in dry dimethylformamide. After stirring for 35 min iodoacetonitrile (0.18 ml) was added and the temperature was raised to 70° C. for 45 min. Then the solvent was removed in vacuo. The residue was triturated with water (30 ml) and filtered. The filter cake was dried, stirred with a mixture of ether (5 ml) and petroleum ether (10 ml) for 1 h, filtered off and dried to give the title compound as white needles. Yield 0.52 g (81%), mp 173.5-174° C., 1H-NMR(DMSO-d6) δ (ppm): 9.69 (s, 1H); 8.06-7.87 (m, 3H); 5.37 (s, 2H), 2.16 (s, 3H); 13C-NMR (DMSO-d6) δ (ppm): 169.6, 136.6, 136.4, 130.5, 129.8, 129.5, 128.5, 112.0, 44.9, 24.3; IR(KBr) ν (cm−1): 3343(NH), 2258(CN), 1682(C═O), 1330(SO2), 1156 and 1140 (SO2).

Provenance & Evidence