Cyanamide → HCID 25140618, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 174 (0.77 g, 4.0 mmol) and cyanamide (0.68 g, 16.0 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (5 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) and filtered. The precipitate was washed with water (3×20 mL), washed with ether (10 mL) and dried. The residue was purified by chromatography, eluting with 5% MeOH/DCM, to give amine 175 (0.30 g, 35%) as a yellow powder: mp (MeOH/DCM) 270-274° C.; 1H NMR [(CD3)2SO] δ 7.83 (s, 1H, H-10), 7.23 (s, 1H, H-5), 7.11 (br s, 2H, NH2), 2.82-2.89 (m, 4H, H-6, H-9), 1.72-1.77 (m, 4H, H-7, H-8); 13C NMR [(CD3)2SO] δ 159.8, 146.9, 146.8, 136.2, 128.0, 124.0, 118.1, 29.1, 28.5, 22.0, 21.8. Anal. calcd for C11H12N4O.¼H2O: C, 59.9; H, 5.7; N, 25.4. Found: C, 60.4; H, 5.5; N, 25.5%.

Provenance & Evidence