4-Toluenesulfonyl chloride → 5,11-Dihydro-5-[2-(4-methylphenylsulfonyl)oxyethyl]dibenzo [b,e][1,4]oxazepine

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Reaction Steps

0.99 g (4.1 mmol) of 5,11-dihydro-5-(2-hydroxyethyl) dibenzo[b,e][1,4]oxazepine was dissolved in 6 ml of anhydrous pyridine. 0.94 g (4.9 mmol) of p-toluenesulfonyl chloride was added to the obtained solution, and they were stirred at room temperature for 6 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane. The obtained solution was washed with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution successively. After drying, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with ethyl acetate and hexane (1:3). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-(4-methylphenylsulfonyl)oxyethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (1.25 g, 76.6%).

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