4-Chlorobenzoyl chloride → Ethyl 1-[(4-chlorobenzoyl)amino]cyclopropanecarboxylate

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Reaction Steps

Add ethyl 1-aminocyclopropanecarboxylate (89.2 g, 0.54 mol) to diisopropylethylamine (187.86 mL, 1.08 mol) in dichloromethane (900 mL) Immerse the flask in a cold water bath and slowly add 4-chlorobenzoic acid chloride (75.46 mL, 0.59 moles). After addition is complete, remove the bath, allow the reaction to equilibrate to 20° C., and stir for approximately 2 hours. Wash with 1N hydrochloric acid (HCl), followed by saturated sodium bicarbonate (NaHCO3), water, and then brine. Dry the organic layer over sodium sulfate (Na2SO4), filter, and concentrate under reduced pressure. Slurry the residue with heptane, filter, and rinse with heptane to give the title compound (142 g, 98%) as a white powder: MS (m/z): 268 (M+1).

Provenance & Evidence