P-Phenylenediamine → Benzyl N-(4-aminophenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

1,4-Phenylenediamine (10 g, 0.093 mol) was stirred rapidly in dichloromethane (800 mL) with diisopropylethylamine (16 mL, 0.093 mol) and the solution cooled to 0° C. A solution of benzyl chloroformate (13 mL, 0.093 mol) in dichloromethane (100 mL) was added very slowly via a dropping funnel. The reaction was left to warm to room temperature over 16 h and concentrated in vacuo. The remaining residue was purified by column chromatography on silica eluting with ethyl acetate/petroleum ether (using a gradient from 25% to 80%) to give 1 as a cream solid (15.5 g, 69.6%). 1H NMR (CDCl3, 400 MHz) δ 3.56 (s(br), 2H, NH2), 5.18 (s, 2H, CH2), 6.45 (s(br), 1H, NH), 6.64 (d, 2H, J=8.8 Hz, ArH), 7.15 (d, 2H, J=6.9 Hz, ArH), 7.36 (m, 5H, ArH).

Provenance & Evidence