Ammonia → 9-Cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin

Participants

Reaction Steps

To 50 ml of N-methylpyrrolidone were added 5.8 g of 9-fluoro-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]-thiepin, 5.4 g of copper cyanide and 0.2 g anhydrous copper sulfate, and the resulting mixture was heated with stirring at 230°-240° C. for 14 hours. After cooling, to the reaction mixture were added 200 ml of 28% aqueous ammonia and 320 ml of water, and the resulting mixture was extracted with benzene. The aqueous and benzene layers were filtered through celite. The collected benzene layer was washed with water several times, diluted hydrochloric acid and then water, which was dried over anhydrous sodium sulfate. The solvent was evaporated to obtain about 6 g of residue which was chromatographed on silica gel. 1.0 g of the starting material was recovered from benzene/chloroform (1/1) eluate and there was obtained from chloroform eluate 9-cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]-thiepin, which was washed with ethanol to give 2.1 g of pale yellow needles having a melting point of 188°-189° C.

Provenance & Evidence