Cyanamide → HCID 25138707, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 238 (2.05 g, 10.6 mmol) and cyanamide (1.78 g, 42.3 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (10 mL) added carefully and the mixture heated at 100° C. for 4 h. The mixture was cooled to 50° C., 7.5 M NaOH solution added until the mixture was strongly basic and the mixture stirred at 100° C. for 3 h. The mixture was cooled, diluted with water (200 mL), filtered, washed with water (3×50 mL) and dried. The aqueous fraction was extracted with CHCl3 (3×50 mL), dried and the solvent evaporated. The combined solids were purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give amine 239 (1.30 g, 56%) as a yellow powder: mp (MeOH/DCM) 280-283° C.; 1H NMR [(CD3)2SO] δ 7.32 (s, 1H, H-10), 7.31 (s, 1H, H-5), 6.96 (br s, 2H, NH2), 4.22 (dd, J=5.3, 5.2 Hz, 2H, H-8), 2.95 (br t, J=6.3 Hz, 2H, H-6), 1.92-1.98 (m, 2H, H-7); 13C NMR [(CD3)2SO] δ 159.1, 152.2, 143.4, 135.8, 128.7, 125.7, 102.6, 66.5, 25.0, 21.0. Anal. calcd for C10H10N4O2: C, 55.0; H, 4.6; N, 25.7. Found: C, 55.1; H, 4.6; N, 25.5%.

Provenance & Evidence