Hydrochloric Acid → 6,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid

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Reaction Steps

7.0 g of 4-(2-chloro-carbonyl-benzyl-thio)phenylacetic acid ethyl ester are dissolved in 30 cc of nitrobenzene and this solution is added dropwise, at room temperature, to a solution of 3.32 g of aluminium chloride in 50 cc of nitrobenzene. The resulting red solution is then heated in an oil bath of 100° for 3 hours. The reaction solution is subsequently poured on a mixture of ice and 10 N hydrochloric acid, is diluted with ether, and the organic phase is separated, washed with water, dried with sodium sulphate, purified with charcoal and filtered. The solvent is completely removed at reduced pressure and the oily residue is dissolved in ether, the ether phase is washed with a 10% sodium bicarbonate solution and then with water, is dried with sodium sulphate, filtered, and the solvent is removed by distillation at reduced pressure. 6,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid ethyl ester crystallizes from ether/pentane. M.P. 96°-97°.

Provenance & Evidence