Diethylamine → N,N-diethyl-2-tert-butylbenzamide

Participants

Reaction Steps

A solution of 2-tert-butylbenzoic acid (4.0 g, 22.5 mmol) in thionyl chloride (8.2 mL, 112 mmol) was stirred at RT for 2 h, then was concentrated three times from carbon tetrachloride to remove all traces of excess thionyl chloride. A solution of diethylamine (4.93 g, 67.4 mmol) in CH2Cl2 (10 mL) was added dropwise over 10 min to an ice water-cooled solution of the crude acid chloride in CH2Cl2 (35 mL). Ten min after addition was complete, the reaction was partitioned between ether and 10% HCl. The ether phase was then washed with sat aq NaHCO3, then was dried (MgSO4), and concentrated to afford a quantitative yield of N,N-diethyl-2-tert-butylbenzamide as an off-white solid. m.p. 38.5-40.5° C.

Provenance & Evidence