1H-1,2,4-Triazole → 1,3-Bis(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3-methylbutan-2-ol

Participants

Reaction Steps

A mixture of 2-(4-chlorophenyl)-2-[2-(1H-1,2,4-triazol-1-yl)prop-2-yl]oxirane (1.1 g.), 1,2,4-triazole (2 g.), potassium carbonate (5 g.) and dry dimethylformamide (25 ml.) was heated at 80° under a nitrogen atmosphere for 16 hours. The reaction mixture was then cooled, filtered, washed with xylene and the filtrate was evaporated in vacuo. The residue was azeotroped with xylene (2×30 ml.) and then partitioned between methylene chloride (50 ml.) and water (50 ml.). The aqueous phase was extracted with methylene chloride (3×50 ml), and the combined organic phases were washed with water (50 ml.), and dried (MgSO4). The residue obtained after removal of the solvent was flash chromatographed on silica (150 g) using methylene chloride/methanol/saturated aqueous ammonia (93:7:1 v/v/v), for elution. The product-containing fractions on evaporation followed by crystallisation from ethyl acetate/hexane yielded 983 mg. (71% yield) of the title compound, m.p. 128°-9°.

Provenance & Evidence