Chlorosuccinimide → HCID 19363330, compound

Participants

Reaction Conditions

Reaction Steps

N-[2-(4-Hydroxyphenyl)ethyl]-4-methoxy-2-methylthio-3-pentyloxybenzamide (85 mg, 0.21 mmol) obtained in Example 2-50, molecular sieve 4A (200 mg) and methylene chloride (1 ml) were mixed, and this mixture was cooled to 0° C. N-Chlorosuccinimide (29.4 mg, 0.22 mmol) was added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered, ethyl acetate (20 ml) was added to the filtrate, and the mixture was washed twice with saturated brine (5 ml). The mixture was dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified twice by column chromatography on silicagel (hene/ethyl acetate=1/1) to give apale-yellow oil. To allow reaction of the residual raw materials, this oil, molecular sieve 4A (200 mg) and methylene chloride (1 ml) were mixed, and cooled to 0° C. N-Chlorosuccinimide (17.4 mg, 0.13 mmol) was added, and the reaction mixture was stirred at room temperature for 2 hours, followed by filtration. Ethyl acetate (20 ml) was added to the filtrate, and the filtrate was washed once with saturated brine (5 ml) and dried over anhydrous magnesium sulfate. Th drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by thin layer chromatography (chloroform/methanol=20/1) to give 2-[2-(4-hydroxyphenyl)ethyl]-6-methoxy-7-pentyloxybenzo[d]isothiazol-3-one (34 mg, 42%) as colorless crystals.

Provenance & Evidence