Thionyl Chloride → Acetonitrile

Participants

Reaction Steps

A benzene (40 ml) solution containing 2 g (8.8 mol) of 3-benzyloxybenzoic acid and 8 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated. A dioxane (10 ml) solution of the resulting residue was added dropwise to a water-dioxane 1:1 (20 ml) solution containing 1.5 g (8.8 mol) of 2-aminobenzenesulfonamide and 1.62 g (19 mol) of sodium bicarbonate, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, dioxane was evaporated, the resulting residue was acidified by adding 1 N HCl under ice-cooling and extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By recrystallizing the resulting residue from acetonitrile 2.0 g (yield: 60%) of the title compound was obtained.

Provenance & Evidence