Hydrochloric Acid → HCID 178506379, compound

Participants

Reaction Conditions

Reaction Steps

4-Trifluoromethoxycinnamonitrile (16.9 g.) was dissolved in a mixture of dry chloroform (50 ml.) and dry methanol (18 ml.). After cooling the solution to 0° C., a stream of hydrogen chloride was passed through the solution until saturation was achieved, then the solution was kept at 0°-5° C. in a refrigerator for four days. Evaporation of the solvents gave a pale yellow solid which was dissolved in absolute ethanol (90 ml.) and treated with formohydrazide (9.01 g.) and triethylamine (23.0 g.). The solution was heated on a steam bath for three and a half hours, then the solvents were evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and dried over magnesium sulphate and the solvent was evaporated to give an orange oil, which was purified by column chromatography, using silica and chloroform/methanol (92:8 v/v) as the element, to give 3-(4-trifluoromethoxystyryl)-1,2,4-triazole, m.p. 125°-127° C.

Provenance & Evidence