Triethylamine → HCID 19874944, compound

Participants

Reaction Conditions

Reaction Steps

Bromopropionylbromide (9.4 mL, 90 mmol) was added dropwise to a cooled (0° C.) solution of 2,6-diisopropylaniline (15.9 g, 89.7 mmol), and triethylamine (12.5 mL, 89.7 mmol) in ethyl acetate (1600 mL). The resulting slurry was warmed (25° C.) and stirred (1.5 hours, 25° C.). The resulting mixture was diluted with ethyl acetate (500 mL), washed with water (1×1000 mL), with 0.5N aqueous HCl (2×600 mL), with saturated aqueous sodium bicarbonate (1×600 mL), with brine (1×600 mL), then dried (MgSO4) and concentrated. The resulting solid was washed with cold ether and dried in a vacuum oven at 40° C. (16 hours) to yield 21.33 g (76.1%) of (±)-N-[2,6-bis(1-Methylethyl)phenyl]-2-bromopropanamide as a white solid.

Provenance & Evidence