Toluene → 1,1'-(1,4-Phenylene)-bis[2-(4-hydroxyphenyl)benzimidazole]

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,4-bis(2-aminoanilino)benzene (28.73g, 0.099 mol), phenyl-4-hydroxybenzoate (42.96g, 0.201 mol), diphenylsulfone (126.45g), and toluene (100 ml) was heated under a nitrogen atmosphere for three hours at 150° C. The toluene was removed and the temperature increased to 290° C. and maintained for two hours. A vacuum was subsequently applied and maintained for one hour. The cooled purple reaction mixture was poured into warm toluene, and the solid recovered by filtration. The crude solid was washed in hot toluene and subsequently dried at 110° C. to afford a purple powder (44.2g, 90% crude yield), mp [Differential Scanning Calorimetry (DSC), heating rate of 10° C./min] sharp peak at 403° C. The solid was recrystallized twice from N,N-dimethylacetamide (DMAc) using charcoal to afford a white powder (26.95g, 55% yield). The compound exhibited a sharp melt by DSC (heating rate of 10° C./min) with a peak at 407° C. Anal. calcd. for (C 32 H22N4O2 : C, 77.72%; H, 4.48%; N, 11.33%; Found: C, 77.48%; H, 4.41%; N, 11.39%.

Provenance & Evidence