N-[5-(hydroxymethyl)-2-methyl-3-thienyl]-N-methylthiophene-2-sulfonamide → N-(5-formyl-2-methyl-3-thienyl)-N-methylthiophene-2-sulfonamide
Reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([CH3:8])=[C:5]([N:9]([CH3:18])[S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH:4]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[S:7][C:6]([CH3:8])=[C:5]([N:9]([CH3:18])[S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:12])[CH:4]=1)=[O:1]Participants
4
Procedure
To a solution of N-[5-(hydroxymethyl)-2-methyl-3-thienyl]-N-methylthiophene-2-sulfonamide (31.1 g) in tetrahydrofuran (300 mL) was added manganese dioxide (43 g), and the mixture was stirred at room temperature overnight. The manganese dioxide was filtered off and the filtrate was concentrated and crystallized from diethyl ether to give N-(5-formyl-2-methyl-3-thienyl)-N-methylthiophene-2-sulfonamide (26.4 g, yield 86%) as yellow crystals.