Triethylamine → HCID 15237344, compound

Participants

Reaction Conditions

Reaction Steps

4,5-Diphenyl-2-oxazolyl-methylformamide (14 g, 0.05 mol) was dissolved in dichloromethane (70 mL)/triethylamine (16 mL) and cooled to about 0° C. under N2. Upon dropwise addition of phosphorous oxychloride (4.7 mL, 0.05 mol), the reaction mixture was warmed to about 25° C. and stirred about 1 hour. A 40% sodium carbonate solution (50 mL) was added and after about 15 minutes the reaction mixture was diluted with water (1 vol), extracted with dichloromethane, washed with saturated sodium carbonate solution, brine and dried (Na2SO4) to give 13 g (98%) of 27 as a white solid. Recrystallization from ether gave light amber colored crystals, mp 95°-96° C. IR (KBr, cm-1) 2970, 2956, 2160 (NC), 1604, 1594, 1502, 1446, 1338, 1212, 1054, 1026, 954, 916, 778, 764, 712, 694, 674, 654, 526. 1H NMR (300 MHz, CDCl3) δ 4.81 (2H, s), 7.31 to 7.41 (7H, m),7.57 to 7.66 (5H, m). 13C NMR (75 MHz, CDCl3) ppm 39.03, 126.78, 127.86, 128.04, 128.58, 128.73, 128.83, 129.25, 131.53, 135.77, 147.28, 153.17, 160.84. m/e 261 (MH+).

Provenance & Evidence