Diisopropylethylamine → HCID 89783700, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-3-bromo-N-ethylbenzamide (2.0 g, 8.23 mmol, 481a), triphosgene (0.830 g, 2.80 mmol, Sigma Aldrich,), DCM (28.0 mL), and DIPEA (1.6 mL, 8.95 mmol) was set stirring at 60° C. with a condenser for 4 h. The mixture was concentrated under reduced pressure to a yellow residue. It was adsorbed onto silica and purified on 24 g SiO2 (eluent: 0-100% EtOAc/hexanes over 25 min, RediSep Gold). The product fractions were combined and concentrated under reduced pressure to give the product as a white solid (736 mg, 98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.52 (1H, s) 7.95 (1H, dd, J=7.82, 1.37 Hz) 7.98 (1H, dd, J=7.82, 1.37 Hz) 7.15 (1H, t, J=7.82 Hz) 3.93 (2H, q, J=7.04 Hz) 1.15 (3H, t, J=7.04 Hz). m/z (ESI, +ve) 268.9 (M+H)+.

Provenance & Evidence