Methyl iodide → 6-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-1,4,4-trimethyl-4H-3,1-benzoxazin-2-one

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Reaction Steps

A solution of 1.1 gm (0.0025 mol) of 6-[4-(3,4-dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 1 ml of methyl iodide in 30 ml of methylene chloride are mixed with 30 ml of 2N sodium hydroxide solution (0.06 mol) and a spatula tip of tetrabutylammonium hydrogen sulfate, and the mixture is stirred for 18 hours at ambient temperature. The organic phase is separated, washed twice with water, and dried with sodium sulfate, and the methylene chloride is distilled off. The residue is purified by column chromatography [silica gel; chloroform/acetone (40:1)]. The uniform fractions are concentrated by evaporation, the residue is stirred with diisopropylether, and the crystal slurry is subjected to suction filtration and dried.

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