[CH2:1]([S:3]([C:5]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]#[N:8])=[O:4])[CH3:2].[OH-:20].[Na+]>C(O)C.O>[CH2:1]([S:3]([C:5]1[CH:12]=[C:11]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]([NH2:8])=[O:20])=[O:4])[CH3:2]To a stirred solution of 2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzonitrile (0.78 g, 2.81 mmol) in ethanol (8.5 ml) is added a 5M solution of sodium hydroxide (8.5 ml) and the mixture is heated at 80° C. for 16 h. After completion of the reaction (monitored by TLC) the reaction mixture is concentrated to get a residue, which is diluted with water (10 ml) and extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with water (10 ml), brine (10 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product which is purified by column chromatography (alumina, 5% methanol/dichloromethane) to yield 2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzamide (0.30 g, 1.01 mmol, 36%).
Loading…
