Cyanamide → HCID 25138704, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 220 (5.55 g, 30.5 mmol) and cyanamide (5.37 g, 122 mmol) were melted together at 100° C., cooled to 50° C., cHCl (15 mL) added dropwise 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 (3×30 mL), washed with ether (3×5 mL) and dried to give 1-oxide 221 (3.24 g, 51%) as a yellow powder: mp (MeOH/DCM) 290-295° C.; 1H NMR [(CD3)2SO] δ 7.45 (s, 1H, H-9), 7.00 (br s, 2H, NH2), 6.94 (s, 1H, H-5), 6.23 (s, 2H, H-7); 13C NMR [(CD3)2SO] δ 160.0, 155.1, 149.0, 147.0, 125.3, 103.1, 101.3, 95.8. Anal. calcd for CBH6N4O3: C, 46.6; H, 2.9; N, 27.2. Found: C, 46.7; H, 2.9; N, 27.3%.

Provenance & Evidence