Hydrochloric Acid → HCID 54274117, compound

Participants

Reaction Steps

138.0 g of 4-chlorobenzenesulfonic acid chloride are added in portions, at room temperature, to a solution of 50.0 g of 3,5-dichloroanthranilic acid ethyl ester in 210 ml of dry pyridine. The reaction mixture is heated to 80°-90° C. and stirred for 28 hours at that temperature to complete the reaction. After cooling, the reaction mixture is poured onto ice/water and acidified with 2N hydrochloric acid. The sticky, oily precipitate is dissolved in diethyl ether, and the aqueous phase is removed. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the ether is evaporated off and the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1. The crystals, which are filtered off, weigh 87.3 g after drying and correspond to the title compound (m.p. 148°-150° C.).

Provenance & Evidence