4-Aminophenol → 4-(1-methyl-4-phenyl-1H-imidazol-2-ylamino)phenol

Participants

Reaction Conditions

Reaction Steps

A slurry of 4-aminophenol (0.227 g, 2.08 mmol), 2-chloro-1-methyl-4-phenyl-1H-imidazole (0.400 g, 2.08 mmol), and p-toluenesulfonic acid monohydrate (0.395 g, 2.08 mmol) was heated in 2.5 mL 2-BuOH in a sealed tube to about 110° C. for 24 h. The temperature was increased to about 120° C. and the solution was heated for 24 h. The reaction was cooled and partitioned between 50 mL pH7 buffer and DCM. The aqueous layer was extracted with DCM (3×), and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting brown oil was purified by silica gel chromatography (0-100% 90/10 DCM/MeOH in DCM) to give 4-(1-methyl-4-phenyl-1H-imidazol-2-ylamino)phenol as a tan solid. MS m/z=266 [M+H]+. Calc'd for C16H15N3O: 265.3.

Provenance & Evidence