Hydrochloric Acid → HCID 20316447, compound

Participants

Reaction Steps

A solution of 950 mg. of 10,11-dihydrodibenzo[b.f]thiepin-2-acetic acid in 50 ml. of methanol is saturated with hydrogen chloride. After 2 hours the reaction mixture is evaporated under reduced pressure and the residue is chromatographed on silica gel using ethyl acetate:hexane (1:7) as eluant to yield methyl 10,11-dihydrodibenzo[b.f]-thiepin-2-acetate (XII, R1 = Me), which is dissolved in 10 ml. of benzene and treated with 900 mg. of 85% m-chloroperbenzoic acid dissolved in 10 ml. of dimethoxyethane. After 5 minutes, 3 ml. of saturated aqueous sodium sulfite is added, followed by 1 ml. of saturated aqueous potassium carbonate. The organic layer is separated, dried with anhydrous magnesium sulfate and filtered through a column of 20 g. of silica gel, eluting with benzene. Evaporation of the eluate under reduced pressure yields a residue which upon recrystallization from chloroform:hexane (1:1) yields 900 mg. of methyl 10,11-dihydrodibenzo[b.f]thiepin-2-acetate-S,S-dioxide (XV, R1 = Me), having a melting point of 103°-105° C.

Provenance & Evidence