Thionyl Chloride → HCID 19028810, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2,4,6-triisopropylphenylsulfonyl)-indole-3-propionic acid (76.22 g) in chloroform (500 ml) was added dropwise thionyl chloride (28.9 ml) at room temperature taking about 10 minutes. The mixture was stirred for one hour at 60° C. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was again added chloroform, followed by concentration under reduced pressure. The concentrate was dissolved in dichloroethane (900 ml). To the solution was gradually added, under ice-cooling, crushed aluminum chloride (58.4 g). The mixture was stirred for 30 minutes, and was added to a mixture of 1N hydrochloric acid (1000 ml) and ice (200 g), followed by extraction with chloroform (900 ml). The extract solution was washed with water (900 ml), dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure. The concentrate was purified by means of a column chromatography (eluted with ethyl acetate:n-hexane=1:4), followed by recrystallization from ethyl acetate-hexane to afford the title compound (43.86 g, m.p.124°-130° C.).

Provenance & Evidence