Hydrochloric Acid → HCID 178506379, compound

Temperature

0 °C

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.

1. customEvaporation of the solvents
2. customgave a pale yellow solid which
3. temperatureThe solution was heated on a steam bath for three and a half hours
4. customthe solvents were evaporated
5. customthe residue was partitioned between ethyl acetate and water
6. customThe organic layer was separated
7. washwashed with water
8. dry with materialdried over magnesium sulphate
9. customthe solvent was evaporated
10. customto give an orange oil, which
11. customwas purified by column chromatography

ORD record

ord-3ec1837eecc24cefbdb1e505f2ae4de9

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04925863