C[O-].[Na+].[NH:4]([CH2:11][CH2:12][C:13]#[N:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:15][NH:16][C:17]1[CH:18]=[C:19]([CH:27]=[C:28]([NH:30][CH3:31])[CH:29]=1)[CH:20](O)CS(C)(=O)=O.CS(C)=O>O>[NH:4]([CH:11]=[C:12]([CH2:20][C:19]1[CH:27]=[C:28]([NH:30][CH3:31])[CH:29]=[C:17]([NH:16][CH3:15])[CH:18]=1)[C:13]#[N:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1A mixture of 8.6 g. of sodium methylate, 12.4 g. of β-anilinopropionitrile and 20.4 g. of 3,5-bis(methylamino)-α-[(methylsulfonyl)methyl]benzyl alcohol in 100 ml. of absolute dimethylsulfoxide was stirred for 1 hour at 50° C. and then treated with 1 liter of water. The precipitated product was extracted with 3 liters of ethyl acetate. The ethyl acetate extract was washed with 1 liter of water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on 1 kg. of silica gel with methylene chloride/ethyl acetate (3:1), there being obtained α-(anilinomethylene)-3,5-bis(methylamino)hydrocinnamonitrile as a brownish-colored oil.
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