[CH3:1][C:2]1[S:6][C:5]([C:7](OC)=[O:8])=[CH:4][C:3]=1[N:11]([CH3:20])[S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:8][CH2:7][C:5]1[S:6][C:2]([CH3:1])=[C:3]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])[CH:4]=1
To a solution of methyl 5-methyl-4-[methyl(2-thienylsulfonyl)amino]thiophene-2-carboxylate (37.5 g) in tetrahydrofuran (200 mL) was slowly added lithium aluminum hydride (4.4 g) in small portions. The reaction mixture was stirred at room temperature for 1 hr, and water (4.4 mL), 15% aqueous sodium hydroxide solution (4.4 mL) and water (13.2 mL) were successively added to the reaction mixture under ice-cooling. The reaction mixture was stirred for 1 hr, and the insoluble material was filtered off. The filtrate was concentrated and crystallized from diethyl ether to give N-[5-(hydroxymethyl)-2-methyl-3-thienyl]-N-methylthiophene-2-sulfonamide (31.1 g, yield 91%) as yellow crystals.
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