Triethylamine → N-Decyl-4-nitrobenzamide

Participants

Reaction Steps

To a solution of 5.4 ml (0.027 mol) of decylamine and 5.6 ml (0.04 mol) of triethylamine in 20 ml of methylene chloride cooled in an ice bath was added dropwise a solution of 5.0 g (0.027 mol) of 4-nitrobenzoyl chloride in 40 ml of methylene chloride. The reaction mixture was stirred in the ice bath for 30 minutes, at room temperature for 15 minutes and kept at 0° for 18 hours. After dilution with methylene chloride, the mixture was washed with 0.5N NaOH and the extract was dried and concentrated to a solid. Recrystallization from methylene chloride-hexane gave 8.1 g (98% yield, mp 89°-91°) of 4-[(decylamino)carbonyl]nitrobenzene. The nmr was consistent with the structure.

Provenance & Evidence