Cyanamide → HCID 25140031, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 156 (17.6 g, 79 mmol) and cyanamide (19.8 g, 471 mmol) were melted together at 60° C. and cHCl (35 mL) was added dropwise. The solution was heated to 100° C., stirred for 1 h, cooled to ca. 50° C. and the mixture made strongly basic with 7.5 M NaOH solution. The mixture was heated to 100° C. for 3 h, cooled to 20° C. and diluted with ice/water. The resulting precipitate was filtered, washed with H2O (100 mL) and Et2O (30 mL), and dried to give 1-oxide 157 (18.4 g, 94%) as a yellow-green solid: mp 230-235° C.; 1H NMR [(CD3)2SO] δ 7.92 (s, 1H, H-9), 7.33 (s, 1H, H-5), 7.11 (br s, 2H, NH2), 4.45 (br s, 1H, OH), 3.49 (t, J=6.6 Hz, 2H, CH2O), 3.06-3.15 (m, 2H, H-6, H-8), 2.59-2.69 (m, 2H, H-6, H-8), 2.49-2.54 (m, 1H, H-7), 1.63 (q, J=6.6 Hz, 2H, CH2); HRMS calcd for C12H14N4O2 (M+) m/z 246.1117, found 246.1115.

Provenance & Evidence