Methyl triflate → 1,5-Dimethyl-2-(4-trifluoromethylphenyl)imidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl trifluoromethanesulfonate (3.3 ml) and p-trifluoromethylbenzonitrile (5.17 g) was heated at 65° C. for 31/2 hours, then cooled to 5° C. The mixture was then dissolved in 10 ml of acetonitrile, and 2 ml of propargylamine in 10 ml of acetonitrile was added. The mixture was stirred at room temperature for 16 hours, then cooled to 5° C. and 3 ml of concentrated sodium hydroxide added (about 1 equivalent), followed by 40 ml of methylene chloride. The organic layer was separated, the solvent evaporated under reduced pressure, and 50 ml of toluene added. The mixture was refluxed for 3 hours, cooled, the solvent evaporated under reduced pressure, and the residue recrystallized from isopropyl ether, to yield 4.6 g of 1,5-dimethyl-2-(4-trifluoromethylphenyl)imidazole, a compound of Formula (6), m.p. 130° C.

Provenance & Evidence