Cyanamide → HCID 25140915, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 203 (4.0 g, 22.2 mmol) and cyanamide (7.2 g, 171 mmol) were mixed together at 80° C., cooled to 50° C., cHCl (8.0 mL) added carefully and the mixture heated at 80° 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 (20 mL), filtered, washed with water (20 mL) and ether (5 mL), and dried to give 1-oxide 204 (8.6 g, 96%) as a yellow powder: mp (DCM) 293-296° C.; 1H NMR [(CD3)2SO] δ 7.71 (s, 1H, H-9), 6.23 (s, 1H, H-5), 4.59 (t, J=8.5 Hz, 2H, H-7), 3.12 (t, J=8.5 Hz, 2H, H-8), NH2 not observed; HRMS (FAB+) calcd for C9H9N4O2 (MH+) m/z 205.0726, found 205.0725.

Provenance & Evidence