Diphenyl N-Cyanocarbonimidate → HCID 178512269, compound

Participants

Reaction Steps

Chart B, Step B-1. To a stirred solution of 3-azido-5-chloroaniline (A-4, 0.706 g, 4.18 mmol) in 6 mL of chloroform, is added diphenyl cyanocarbonimidate (0.997 g, 4.18 mmol). The solvent is allowed to evaporate at a temperature of 75° C. overnight. The resulting solid is triturated with ether and filtered. The solid is recrystallized from ethyl acetate/hexane to afford 0.808 g of N-(3-azido-5-chlorophenyl)-N'-cyanocarbamimidic acid, phenyl ester. (B-1) Mp 193°-194° C. (dec); IR (mull) 3084, 2954, 2925, 2210, 2117, 2104, 1652, 1608, 1581, 1500, 1449, 1438, 1405, 1222, 1197, 1002, 892 cm-1 ; 1H NMR (DMSO) δ10.9 (bs, 1 H), 7.45-7.20 (bm, 8 H), 7.07 (bs, 1 H); 13C NMR (DMSO) δ151.3, 141.5, 138.6, 134.0, 129.8, 126.4, 120.8, 119.4, 116.2, 112.8, 112.5; Analysis calculated for C14H9ClN6O: C, 53.77; H, 2.90; N, 26.87; Cl, 11.34. Found: C, 53.39; H, 2.71; N, 26.54; Cl, 11.32.

Provenance & Evidence