Chloroform → HCID 23337057, compound

Participants

Reaction Steps

The mixture of 1.1 g of 9-chloro-10,11-dihydro-2-ethoxy-11-hydroxydibenzo[b,f]thiepin and 33 ml of thionyl chloride was refluxed for 3 hrs. and evaporated to obtain the residue, to which was added 50 g of ice-water. The resulting mixture was extracted with chloroform and the extract was washed with water and dried over calcium chloride. The solvent was evaporated to obtain the concentrated which was added with stirring at room temperature to a mixutre of 70 ml of anhydrous tetrahydrofuran and 400 mg of lithium aluminum hydride. The thus obtained mixture was refluxed with stirring for 4 hrs., to which was added 30% sodium hydroxide solution with stirring under cooling with a mixture of ice and sodium chloride. The mixture was filtered and the filtrate was evaporated to obtain the residue, to which was added 100 ml of chloroform and 100 ml of water, and the chloroform layer was collected. This was washed with water, dried and the solvent was evaporated to obtain 520 mg of 9-chloro-10,11-dihydro-2-ethoxydibenzo[b,f]thiepin as oily substance.

Provenance & Evidence