N-[5-(hydroxymethyl)-2-methyl-3-thienyl]-N-methylthiophene-2-sulfonamide → N-(5-formyl-2-methyl-3-thienyl)-N-methylthiophene-2-sulfonamide

HRID 453573Notes

Reaction equation

HRID 453573 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

Reactant 1

HCID 59411384N-[5-(hydroxymethyl)-2-methyl-3-thienyl]-N-methylthiophene-2-sulfonamide

Product 1

HCID 59411396N-(5-formyl-2-methyl-3-thienyl)-N-methylthiophene-2-sulfonamideYield 86%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. filtrationThe manganese dioxide was filtered off
  2. concentrationthe filtrate was concentrated
  3. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-b4ba05639ba94863bf1798ca5dc10784
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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