Ethyl Acetate → Acetate

Participants

Reaction Steps

4.3 g (28.7 mmol) of 3-phenylpropylthiol are added dropwise at 0° to a mixture of 1.4 g (31.6 mmol) of sodium hydride dispersion in oil (55%) and 30 ml of tetrahydrofuran. The mixture is then stirred for 30 minutes at 0°. A solution of 4-chloro-N-(bromoacetyl)-anthranilic acid methyl ester in 30 ml of tetrahydrofuran is added dropwise and the mixture is then stirred for one hour at 0° and for three hours at room temperature. Ethyl acetate is added and the reaction mixture is extracted with water and brine. The aqueous phases are washed with ethyl acetate and the organic phases are combined, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexanelethyl acetate (4:1) yields 4-chloro-N-(3-phenylpropylthio)acetylanthranilic acid methyl ester in the form of a yellow oil.

Provenance & Evidence