P-Phenylenediamine → tert-Butyl (4-aminophenyl)carbamate

Participants

Reaction Steps

To a solution of p-phenylenediamine (16.2 g) and triethylamine (20.8 ml) in DMF (80 ml) was added di-tert-butyl carbonate (34.4 ml). The reaction mixture was stirred at room temperature for 8 hr and diluted with ethyl acetate. The ethyl acetate solution was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=4/1 to ethyl acetate), and the resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (29.2 g, 95%).

Provenance & Evidence