Toluene → 2-(4-Cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]thioacetimidate methyl ester

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Reaction Steps

To a suspension of 2-(4-cyanophenylamino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxypheny l]thioacetamide (100 g, 267 mmol) in acetonitrile (600 mL), under water cooling, trimethyloxonium tetrafluoroborate (39.5 g, 267 mmol) was added over 20 minutes, and the resulting mixture was stirred at room temperature for 0.5 hours. To the solution, under water cooling, manganese dioxide (139 g, 1.602 mmol) was added over 10 minutes, and the resulting mixture was stirred at room temperature for 1 hour. Toluene (500 mL) was added to the reaction mixture, and the resulting mixture was filtered, after which the resulting filter cake was washed with ethyl acetate. The filtrate obtained and a washing solution were combined, and the resulting mixture was sequentially washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated saline, dried over anhydrous magnesium sulfate, and then filtered. The filtrate obtained was concentrated under reduced pressure to obtain a crude product of the captioned compound as an oily product.

Provenance & Evidence