5-(4-Hydroxymethylbenzoyl)-3-thiophene sulfonamide → 5-(4-Formylbenzoyl)-3-thiophene sulfonamide

HRID 1463260Notes

Reaction equation

HRID 1463260 reaction equation
[OH:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[S:13][CH:12]=[C:11]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:10]=2)=[O:8])=[CH:5][CH:4]=1>O=[Mn]=O.C1COCC1>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[S:13][CH:12]=[C:11]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:10]=2)=[O:8])=[CH:18][CH:19]=1)=[O:1]

Participants

4

Reactant 1

HCID 108278525-(4-Hydroxymethylbenzoyl)-3-thiophene sulfonamide

Product 1

HCID 107562885-(4-Formylbenzoyl)-3-thiophene sulfonamide

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

30 mg (0.1 mmol) of 5-(4-hydroxymethylbenzoyl)-3-thiophene sulfonamide and 300 mg of MnO2 were added to 5 mL of THF. After stirring at rt for 30 min the mixture was filtered through a bed of celite and eluted with ethyl acetate. The filtrate was concentrated and the crude product subjected to flash chromatography utilizing 1:1 ethyl acetate/hexane as the eluent to recover 16 mg of 5-(4-formylbenzoyl)-3-thiophene sulfonamide as a yellow solid.

Workup

  1. filtrationwas filtered through a bed of celite
  2. washeluted with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customto recover 16 mg of 5-(4-formylbenzoyl)-3-thiophene sulfonamide as a yellow solid

Sources & evidence

ORD record
ord-caf9fe66209840a6bc9ffb1409ff4ee3
Source dataset
uspto-grants-1994_04
Patent number
US05300499

Reaction notes

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