Pyridine → 1,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole

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To a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (0.92 g, 3.95 mmol) in 10 mL of dioxane, were added pyridine (0.319 mL, 3.95 mmol) and a solution of 4-methoxybenzoyl chloride (673 mg, 3.95 mmol) in 3 mL of dioxane. The mixture was refluxed with stirring for 12 hours. The solvent was removed under reduced pressure. 50 mL of dichloromethane and 20 mL of 0.1 N hydrochloric acid were added to the residue and the organic layer was separated. The aqueous layer was extracted with 50 mL of dichloromethane. A combined organic layer was washed with 0.1 N hydrochloric acid and brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (toluene-ethyl acetate 9:1) and then recrystallized with diisopropyl ether-hexane to give pale brown needle of 1,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (0.67 g, 48.6% yield).

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