[C-]#N.[Na+].C(O)C.[C:7]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])#[N:8].[CH3:17][S:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1>O>[C:7]([C:9]1[CH:10]=[C:11]([C:12](=[O:13])[CH:23]([OH:24])[C:22]2[CH:25]=[CH:26][C:19]([S:18][CH3:17])=[CH:20][CH:21]=2)[CH:14]=[CH:15][CH:16]=1)#[N:8]Sodium cyanide (3 mmol, 0.147 g) was added to a mixture of ethanol (30 ml), water (30 ml), 3-cyanobenzaldehyde (30 mmol, 3.93 g) and 4-(methylthio)benzaldehyde (30 mmol, 4.0 ml). The reaction was stirred at reflux 30 minutes, diluted with water (20 ml) and extracted with ethyl acetate (250 ml). The organic layer was separated, dried over magnesium sulfate, concentrated, and the residue purified by silica gel chromatography (2:1 hexane:ethyl acetate), affording the title compound as a solid (5.2, 61%).
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