Acetyl chloride → HCID 178491162, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-(3,4-dimethoxybenzyl)-2-(cis-4-hydroxycyclohexylamino)-5-nitrobenzamide (1.0 g) in dichloromethane (20 mL) were added triethylamine (0.49 mL) and 4-dimethylaminopyridine (284 mg), and then acetyl chloride (0.20 mL) at 20° C. The reaction mixture was stirred for 2 hours at 20° C. and then, acetyl chloride (0.05 mL) was added. After stirring for an hour at 20° C., the reaction mixture was partitioned between chloroform and 1N-hydrochloric acid. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and hexane (1:2). The residual solid was recrystallized from ethyl acetate to give 2-[cis-4-(acetoxy)cyclohexylamino]-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (429 mg) as yellow crystals.

Provenance & Evidence