Dibenz(b,f)azepine → 5H-Dibenz(b,f)azepine-5-carbonitrile

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Reaction Steps

By a procedure analogous to that described in Example 1, 97.0 g of 5H-dibenz[b,f]azepine are suspended in 320 ml of 1,2-dichloroethane, and 2 ml of N,N-dimethylacetamide are added. The temperature is raised to 60°, and 50 g of cyanogen chloride are introduced in the course of 2 hours, the reflux condenser being cooled to -17° in order to avoid loss of cyanogen chloride. The mixture is kept at 60° for 16 hours; a descending condenser is then fitted, and at normal pressure 200 ml of a mixture of cyanogen chloride and 1,2-dichloroethane are distilled off into a cooled receiver. During distillation, the 1,2-dichloroethane passing over is continuously replaced by fresh solvent in order to remove residual cyanogen chloride. The contents of the flask are cooled to room temperature; 200 ml of water are added, and the mixture is rendered permanently alkaline by the addition of 30% sodium hydroxide solution. Further processing, analogous to that in Example 2, yields 96.3 g of 5-cyano-5H-dibenz[b,f]azepine, which, according to the IR spectrum, is identical to authentic material; m.p. 108°-109°. A further 4 g of final product can be obtained from the mother liquor, and the total yield is 100.3 g (92% of theory).

Provenance & Evidence