4-Fluorobenzonitrile → 4-[n-(1h-Imidazol-1-yl)-n-(4-trifluoromethylphenyl)amino]benzonitrile

Participants

Reaction Steps

To a cold solution (10-15° C.) of tBuOK (1.06 g, 0.00895 mol) in DMSO (18 ml) was added portionwise N-(1H-imidazol-1-yl)-4-trifluoromethylaniline (1.85 g, 0.00814 mol) (prepared by desulfurization from the corresponding 2,3-dihydro-1H-imidazol-2-thione, J. G. Schantl, Heterocycles, 37(3), 1873, 1994). The reaction mixture was stirred at room temperature for 1 h, then 4-fluorobenzonitrile (0.936 g, 0.00773 mol) in DMSO (18 ml) was added, the reaction mixture was stirred for 2 h and pourred into water and concentrated sodium hydroxyde solution. The precipitate was collected and dried under vacuum. Flash chromatography on silica gel (toluene/dioxane: 7/3) and crystallization from diisopropyl ether yielded a solid (1.6 g, 60%), mp 104° C.

Provenance & Evidence