Cyanamide → HCID 25139615, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-nitroaniline 254 (510 mg, 2.5 mmol) and cyanamide (460 mg, 10.9 mmol) was melted at 100° C. The mixture was cooled to 60° C. and cHCl (4 mL) was added slowly. The solution was heated at 100° C. for 1 h, then three more aliquots of cyanamide (460 mg, 10.9 mmol) and cHCl (5 mL) were added over 3 h. The solution was cooled to 60° C. and the solution made basic with NaOH solution (7.5 M, 10 mL). The solution was heated at 100° C. for another 1 h, cooled and diluted with water (50 mL). The solid was filtered and washed with water (30 mL) to give 1-oxide 262 (360 mg, 63%) as a brown solid: mp 226-229° C.; 1H NMR [(CD3)2SO] δ 7.50 (d, J=8.6 Hz, 1H, H-5), 7.32 (d, J=8.6 Hz, 1H, H-6), 7.09 (br s, 2H, NH2), 4.09 (s, 2H, H-10), 2.88 (t, J=5.7 Hz, 2H, H-7), 2.58 (t, J=5.7 Hz, 2H, H-8), 2.40 (s, 3H, NCH3); MS (APCI) m/z 232 (MH+, 100%). Anal. calcd for C11H13N5O.¼CH3OH: C, 56.5; H, 5.9; N, 29.3. Found: C, 56.6; H, 5.6; N, 29.1%.

Provenance & Evidence