Water → HCID 13508159, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen and in glassware dried with a heat gun, a solution of 0.9 g (3 mmole) of 4,5-diphenyl-1-(2-tetrahydropyranyl)imidazole in 15 ml THF and 15 ml ether was chilled to -78° C. To the cold solution was added dropwise a solution of 2.5 ml (4 mmole) of 1.6 M n-butyl lithium in hexane in 10 ml ether. The solution was stirred at -78° C., then 0.55 g (4 mmole) of trifluoromethanesulfenyl chloride (TOXIC) was added as a gas. The mixture was stirred at -78° C. for 2 hours, then at RT overnight. The mixture was poured into water and extracted with ether (pH of aqueous layer ~4). The aqueous layer was neutralized with bicarbonate then extracted with more ether. The combined ether extracts were dried and concentrated. The crude residue was chromatographed on 50 g SilicAR CC-7, eluting with 98% toluene/2% ethyl acetate, to give 0.45 g (47%) of product. Recrystallization from toluene gave 0.3 g (31%) of white solid, mp 254°-6°. ; Anal. Calc'd. for C16H11F3N2S: C, 59.99; H, 3.46; N, 8.75. Found: C, 60.20; H, 3,57; N, 8.52.

Provenance & Evidence