Sodium Sulfite → N-(2-t-Butyl-5-carbamoylphenyl)-3-(5-chloro-2,4-dimethoxyphenyl)octanamide

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Reaction Conditions

Reaction Steps

181 mg (1.36 mmol) of N-chlorosuccinimide were added to a solution of 504 mg (1.11 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Example 2) in a mixture of 10 ml of acetonitrile and 4 ml of methylene chloride, and the resulting mixture was stirred at 50° C. for 15 hours. At the end of this time, the reaction mixture was allowed to cool to room temperature, after which a 1M aqueous solution of sodium sulfite was added to decompose any excess of the reagent. The mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel using ethyl acetate as the eluent, to give 434 mg (yield 80%) of the title compound as crystals, melting at 161.5-163.5° C. (from ethyl acetate-isopropyl ether).

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