N,N-Dimethylbenzamide → HCID 22555997, compound

Participants

Reaction Steps

While cooling in a dry ice/isopropanol bath, to a solution of 1 (3.00 g, 13.2 mmol) in tetrahydrofuran at −78° C. was added dropwise n-butyllithium (2.5M in hexanes, 11.1 mL, 27.8 mmol). After stirring for 0.5 h the reaction mixture was warmed over 0.5 h to −15° C. It was recooled in the IPA/dry ice bath then a tetrahydrofuran solution of N,N-dimethylbenzamide (2.38 g, 15.8 mmol) was added. The reaction mixture was warmed to room temperature and quenched with water. The solvent was removed in vacuo. Sat. sodium bicarbonate was added and the mixture extracted with ethyl acetate (3×). The combined organic portions were dried with sodium sulfate (anh.), filtered, and concentrated. A solid resulted. It was triturated with ether to give 2 as a white solid (3.11 g, 71%)

Provenance & Evidence