tert-Butanol → N-t-butyloxycarbonyl-3,5-dinitro-4-methylaniline

Participants

Reaction Steps

A mixture of 3,5-dinitro-p-toluic acid (20 g), diphenylphosphoryl azide (29.2 g) and triethyl amine (10.7 g, from Mallinckrodt) in tert-butyl alcohol (200 mL) under nitrogen was heated at reflux for 1 hr. The solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate (300 mL) and 1N HCl (300 mL). The ethyl acetate solution was washed with half-saturated sodium chloride solution, 1N sodium hydroxide solution (300 mL), and dried over magnesium sulfate. The solvent was evaporated and the residue was chromatographed on silica gel eluting with ethyl acetate:hexane (1:9) to afford N-t-butyloxycarbonyl-3,5-dinitro-4-methylaniline (7.8 g).

Provenance & Evidence