Triethylamine → 1-(4-Chlorophenyl)cyclopropanecarbohydrazide

Participants

Reaction Steps

A solution of 1-(4-chlorophenyl)-1-cyclopropanecarboxylic acid (9.83 g, 50 mmol), tert-butyl carbazate (7.93 g, 60 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.54 g, 55 mmol), 1-hydroxybenzotriazole monohydrate (7.43 g, 55 mmol), and triethylamine (12.65 mL, 125 mmol) in N,N-dimethylformamide (100 mL) was stirred overnight at room temperature. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. A 4 M solution (62.5 mL) of hydrochloric acid in 1,4-dioxane and methanol (200 mL) were added to the partially purified product, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, dichloromethane was added to the residue, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, hexane was added to the obtained partially purified product, and the solid was collected by filtration to obtain the title compound (9.06 g, 86%) as a light brown solid.

Provenance & Evidence