1H-1,2,4-Triazole → HCID 13457303, compound

Participants

Reaction Steps

2,2,2-Trifluoro-4'-chloroacetophenone (0.8 g, 3.84 mmole), trimethylsulphoxonium iodide (1.02 g, 4.6 mmole) and cetyltrimethylammonium bromide (0.1 g, 0.27 mmole) were stirred in a mixture of 1,1,1-trichloroethane (40 ml) and 18% sodium hydroxide solution (20 ml) at 75° for 2 hours. The mixture was then allowed to cool, the organic layer was separated, evaporated, and the residue was stirred in dimethylformamide (50 ml) with 1,2,4-triazole (1 g, 14.5 mmole) and anhydrous potassium carbonate (2 g, 14.5 mmole) at 90° for 4 hours. The mixture was then allowed to cool, ethyl acetate (100 ml) and water (50 ml) were added and the aqueous layer was separated. The organic layer was washed a further 6 times with water (200 ml in total), dried over magnesium sulphate, and evaporated to give a gum (104 mg) which was chromatographed on silica (230-400 mesh), eluting with ethyl acetate to give as a colorless solid the title compound, 84 mg (8%). One recrystallization from dichloromethane/hexane gave colorless crystals, 64 mg, m.p. 117°-118° C.

Provenance & Evidence