Cyanamide → HCID 25140756, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 185 (2.26 g, 11.0 mmol) and cyanamide (1.84 g, 43.8 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 (100 mL), filtered, washed with water (3×20 mL), washed with ether (10 mL) and dried. The residue as purified by chromatography, eluting with 5% MeOH/DCM, to give amine 186 (0.26 g, 10%) as a yellow powder: mp (MeOH) 261-265° C.; 1H NMR [(CD3)2SO] δ 7.86 (s, 1H, H-11), 7.29 (s, 1H, H-5), 7.13 (br s, 2H, NH2), 2.84-2.90 (m, 4H, H-6, H-10), 1.74-1.80 (m, 2H, H-8), 1.58-1.67 (m, 4H, H-7, H-9); 13C NMR [(CD3)2SO] δ 160.2, 152.8, 147.8, 141.2, 127.9, 124.3, 117.8, 35.6, 35.1, 31.3, 29.3, 28.0. Anal. calcd for C12H14N4O: C, 62.6; H, 6.1; N, 24.3. Found: C, 62.9; H, 6.2; N, 24.6%.

Provenance & Evidence