p-Toluenesulfonic acid → HCID 57470286, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL flask was charged with 4.8 g (24 mmol) of N-(2,6-dichlorophenyl)acetamidine, sodium bicarbonate 4.03 g (48 mmol) and 250 mL anhydrous ethanol. 5 g (26.2 mmol) of 3-bromo-1,1,1-trifluoro-propan-2-one was added dropwise. After 1 h solid was filtered off and the filtrate was evaporated in vacuo to give a crude. A mixture of the crude and p-toluenesulfonic acid (668 mg, 3.5 mmol) in toluene was heated to 105° C. for 15 hours. The crude reaction mixture was washed into a separatory funnel with ethyl acetate and water. The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo to give the crude product, which was then purified by column chromatography on silica eluting with EtOAc-Hexane (10:0 to 3:2) to afford 1-(2,6-dichloro-phenyl)-2-methyl-4-trifluoromethyl-1H-imidazole as a tan solid (0.9, 43%); 1H NMR (400 MHz, CDCl3): δ 7.52 (m, 2H), 7.43 (m, 1H), 7.19 (m, 1H), 2.2 (s, 3H); MS (ES): 295 [M+H]+.

Provenance & Evidence