Cyanamide → HCID 25140751, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 169 (0.73 g, 3.8 mmol) and cyanamide (0.63 g, 15.1 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (5 mL) added carefully and the mixture heated at 100° C. for 2 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 (50 mL), filtered, washed with water (2×25 mL) and dried. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give amine 170 (124 mg, 15%) as a yellow powder: mp (MeOH) 271° C. (dec.); 1H NMR [(CD3)2SO] δ 7.43 (d, J=8.6 Hz, 1H, H-6), 7.26 (d, J=8.6 Hz, 1H, H-5), 7.00 (br s, 2H, NH2), 3.36-3.40 (m, 2H, CH2), 2.75-2.80 (m, 2H, CH2), 1.67-1.75 (m, 4H, 2×CH2); 13C NMR [(CD3)2SO] δ 159.5, 149.5, 137.3, 133.8, 131.1, 129.9, 123.0, 29.8, 28.7, 22.5, 21.0. Anal. calcd for C11H12N4O: C, 61.1; H, 5.6; N, 25.9. Found: C, 61.0; H, 5.6; N, 26.0%.

Provenance & Evidence