Cyanamide → HCID 11952364, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of nitroaniline 123 (4.43 g, 17.8 mmol) and cyanamide (3.51 g, 83.6 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (8.21 mL) added carefully and the mixture stirred at 65-70° C. for 90 min. A solution of 7.5 M NaOH (72 mL) was added until the mixture was strongly basic and the mixture stirred at 90-98° C. for 45 min. The mixture was cooled, diluted with water (50 mL), filtered, washed with water (3×20 mL) and dried to give 1-oxide 124 (3.67 g, 89%) as a green-yellow solid: mp (DCM/MeOH) 255-257° C.; 1H NMR [(CD3)2SO] δ 7.93 (s, 1H, H-9), 7.33 (s, 1H, H-5), 7.10 (s, 2H, NH2), 4.67 (t, J=5.2 Hz, 1H, OH), 3.40 (dd, J=6.5 Hz, 5.2 Hz, 2H, CH2O), 2.99-3.10 (m, 2H, CH2), 2.73-2.85 (m, 2H, CH2), 2.52-2.63 (m, 1H, CH); 13C NMR [(CD3)2SO] δ 159.9, 153.5, 148.6, 141.9, 128.8, 120.1, 114.1, 63.7, 41.6, 35.3, 34.6. Anal. calcd for C11H12N4O2.¼CH3OH: C, 56.2; H, 5.5; N, 23.3. Found: C, 56.7; H, 5.4; N, 23.2%.

Provenance & Evidence