Ethyl Acetate → 4-Acetamido-4'-aminoazobenzene

Participants

Reaction Steps

Following the general monoacylation procedure, 4,4′-azodianiline (25 mg, 120 μmol) was treated with acetyl choloride (8.5 μl, 120 μmol). Silica gel chromatography through a wide column (20% ethyl acetate in dichloromethane, gradient to 66%) provided S1 as an orange solid (22 mg, 90 μmol, 73% yield): 1H (CD3CN, 500 MHz): 1.98 (s, 3H); 4.77 (s, 2H); 6.74 (d, 2H, J=8.5); 7.70 (d, 4H, J=8.5); 7.77 (d, 2H, J=8.5); 8.53 (s, 1H). 13C (CD3CN, 125 MHz): 23.4, 113.9, 119.3, 122.7, 124.7, 140.6, 144.3, 148.6, 151.5, 168.7. HRMS (FAB+): calc'd for C14H14N4O—254.1168, found—254.1171 (M+).

Provenance & Evidence