Thionyl Chloride → N-Cyclopropyl-3-iodo-4-methylbenzamide

Participants

Reaction Steps

To 3-iodo-4-methylbenzoic acid (3.5 g, 13 mmol) was added thionyl chloride (10 mL) before heating the mixture to reflux for 1.5 h. The reaction mixture was concentrated in vacuo, and dissolved in DCM (50 mL) and Hunigs base (4.6 mL, 27 mmol). After the addition of cyclopropylamine (1.87 mL, 27 mmol) at −78° C., the reaction mixture was stirred at ambient Temp. for about 3 h. The mixture was diluted with 100 mL DCM, washed with 20 mL saturated, aqueous NaHCO3 and 20 mL 3 N HCl, and dried over anhydrous Na2SO4. The solid obtained was suspended in EtOAc and filtered to give the title compound. MS (ES+): 302 (M+H)+.

Provenance & Evidence