1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66621468, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-nitrophenyl)benzo[d]oxazole-4-carboxylic acid (1.42 g, 5 mmol) in DMF (70 mL) was added HOBt (0.75 g, 5.5 mmol), NH4Cl (0.27 g, 5.0 mmol), DIPEA (1.94 g, 15.0 mmol) and EDCI (1.15 g, 6.0 mmol). The mixture was stirred at 30° C. for 17 hr. To the resulting mixture, water (10 mL) was added and 1N aqueous hydrochloric acid to pH=3, then filtered, the filtrate was washed with saturated sodium bicarbonate solution (100 mL×2), brine (100 mL×2) and dried in vacuum to get a crude product. The crude product was re-crystallized in THF to obtain 2-(3-nitrophenyl)benzo[d]oxazole-4-carboxamide as a yellow solid (700 mg, yield 49%); LC-MS (ESI) m/z 284 [M+1]−.

Provenance & Evidence