1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18354634, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-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 18 hr. The resulting mixture was purged in water (10 mL) and aqueous hydrochloric acid (1 N) to pH=3, then filtered, and the filtrate was washed with saturated sodium bicarbonate solution (100 mL×2) and brine (100 mL×2), and dried in vacuum to obtain the crude product. Re-crystallization in THF obtained 2-(4-nitrophenyl)benzo[d]oxazole-4-carboxamide as a yellow solid (800 mg, yield 56%). LC-MS (ESI) m/e 284 [M+1]+.

Provenance & Evidence