Carbon Dioxide → HCID 19889059, compound

Participants

Reaction Conditions

Reaction Steps

To 1.5 g (6.2 mmol) of 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thiol and 1.5 g (10.9 mmol) of powdered potassium carbonate stirring in 20 ml of dimethylformamide, 3 ml of condensed trifluoromethyl iodide was added dropwise at ambient temperature. Keeping the dry ice condenser on from the addition, the stirred mixture was warmed to 30° C. At three separate times during a 2 h period, 2.0 ml portions of trifluoromethyliodide were added. Excess water was added and the aqueous mixture was extracted with a 1:1 mixture of ethyl acetate/diethyl ether (200 ml) and the organic layer was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Silica gel column chromatography (methylene chloride followed by 1:1 methylene chloride/ethyl acetate) afforded 0.4 g of the title compound (main component present), m.p. 91°-93° C.

Provenance & Evidence