Cyclopropanecarbonyl chloride → HCID 67311146, compound

Participants

Reaction Steps

To a solution (100 mL) of methyl 3-[(2-amino-1,3-benzooxazol-6-yl)oxy]benzoate (6.84 g, 24.1 mmol) in pyridine were added N,N-dimethylpyridine-4-amine (129 mg, 1.05 mmol) and cyclopropanecarbonyl chloride (2.5 mL, 27.5 mmol), and the mixture was stirred at room temperature for 1.5 hr. To the reaction mixture was added cyclopropanecarbonyl chloride (2.5 mL, 27.5 mmol), and the mixture was further stirred at room temperature for 1.5 hr. Cyclopropanecarbonyl chloride (1.5 mL, 16.5 mmol) was further added to the reaction mixture, and the mixture was continuously stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate (200 mL). This suspension was washed with 0.1N hydrochloric acid (150 mL) and saturated aqueous sodium hydrogencarbonate solution (150 mL), successively. The diluted hydrochloric acid layer was extracted with ethyl acetate (100 mL×2), and the combined organic layers were washed with saturated aqueous sodium hydrogencarbonate solution (150 mL) and saturated brine (150 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give a brown amorphous substance (8.2 g).

Provenance & Evidence