Cyanogen Bromide → HCID 10926720, compound

Participants

Reaction Steps

N-(5-Chloro-2-methoxyphenyl)-4-(trifluoromethyl)benzene carbohydrazonamide (1.5 g, 4.36 mmol) was dissolved in 1,4-dioxane (7 ml) and cyanogen bromide (475 mg, 4.48 mmol) was added. A solution of sodium bicarbonate (380 mg in 7 ml of water) was added dropise at room temperature and the reaction mixture was stirred for 3 h. An additional 7 ml of water was added to the heterogenous reaction mixture before filtration and rinse with water. Recrystallization from acetonitrile gave 922 mg (57.3%) mp 247-248° C.; IR(KBr, υ=cm−1) 3416, 3076, 3052, 1652, 1561, 1504, 1322, 1110; 1 H NMR (300 MHz, DMSO-d6) δ 3.60 (3H, s), 5.92 (2H, s), 7.22 (1H, d, J=9.5 Hz), 7.47 (2H, d, 8.3 Hz), 7.54-7.57 (2H, m), 7.67 (1H, d, J=8.4 Hz).; MS(DCl)m/z: 369(MH+). Anal. calcd. for C16H12ClF3N4O: C, 52.12; H, 3.28; N, 15.19. Found: C, 52.19; H, 3.20; N, 15.29.

Provenance & Evidence