Benzonitrile → Kyaphenine

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Benzonitrile (5.2 g, 0.05 mol) was added dropwise over a period of 100 sec to 20 ml (34 g, 0.23 mol) of stirred trifluoromethanesulfonic acid with the temperature being allowed to rise as high as 91°C. When the reaction mixture cooled to 25°C, the yellow solution was poured into 100 ml cold ethanol. The yellow color disappeared and a white flocculent precipitate formed. Recrystallization of this precipitate from 150 ml chloroform afforded 3.43 g (66 percent yield) of 2,4,6-triphenyl-s-triazine (white crystals, m.p. 235°-237°C) (Lit. m.p. 232°C, J. Chem. Soc., 1941, 278). The 3.43 g sample of product exhibited no nitrile bands in the infrared spectrum but the infrared spectral band characteristic of the triazine structure was very strong at 6.6μ.

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