Aniline → HCID 23156213, compound

Participants

Reaction Steps

Compound 34 (0.300 g, 1.01 mmol) was dissolved in dichloromethane (10 mL), and triethylamine (0.284 mL, 2.03 mmol) and methanesulfonyl chloride (0.118 mL, 1.52 mmol) was added to the solution at 0° C., followed by stirring for 1.5 hours. The reaction mixture was added with water to decompose excess reagent, and diluted with chloroform, then washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Then, the residue was dissolved in dichloromethane (10 mL), triethylamine (0.283 mL, 2.03 mmol) and aniline (0.277 mL, 3.04 mmol) was added to the solution, followed by stirring at room temperature overnight. The reaction mixture was diluted with chloroform, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3). The desired compound was crystallized from diisopropyl ether to obtain Compound 35 (0.149 g, yield 40%).

Provenance & Evidence