Benzoyl chloride → HCID 25096340, compound

Participants

Reaction Steps

To a stirred solution of benzoyl chloride (42 mg, 0.3 mmol) in acetone (3.0 mL) was added ammonium thiocyanate (68 mg, 0.9 mmol). The resulting mixture was stirred for 1 h at room temperature followed by addition of the indoline compound 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole (100 mg, 0.3 mmol). After stirred overnight at room temperature, the reaction mixture was quenched with excess saturated ammonium chloride (30 mL) and extracted with ethyl acetate (30 mL×3). The organic layers were combined, washed with brine, and then concentrated under vacuum. The residue was purified by silica gel chromatography to give N-{4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioyl}-benzamide (74 mg, 0.15 mmol, 50%) as a white solid. MS (EI): m/z 495 (M+H).

Provenance & Evidence