O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Participants

Reaction Steps

TEA (21.7 mL; 156 mmol) was added to a mixture of 1-(trifluoromethyl)-cyclopropanecarboxylic acid (8.00 g; 51.9 mmol) and TBTU (16.7 g; 52 mmol) in DMF (40 mL). After 1 h at rt, a solution of (4-chloro-3-nitrophenyl)methylamine hydrochloride (11.6 g; 52 mmol) in DMF (70 mL) was added dropwise over 30 min. After 17 h at rt, the mixture was concentrated and the residue partitioned between water and MTBE. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give the sub-title compound. Yield: 13.191 g (78%).

Provenance & Evidence