5-Bromo-4-methylthiophene-2-sulfonamide → 4-Methylthiophene-2-sulfonamide

HRID 6960Notes

Reaction equation

HRID 6960 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][C:3]=1[CH3:11]>CC(O)=O.[Zn]>[CH3:11][C:3]1[CH:4]=[C:5]([S:7]([NH2:10])(=[O:9])=[O:8])[S:6][CH:2]=1

Participants

4

Reactant 1

HCID 220195335-Bromo-4-methylthiophene-2-sulfonamide

Product 1

HCID 6009294-Methylthiophene-2-sulfonamideYield 43%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 5-bromo-4-methylthiophene-2-sulfonamide (3.1 g, 12.1 mmol) in AcOH (30 mL) is added zinc dust (2.4 g, 36.2 mmol). The reaction mixture is heated to reflux for 8 hr. After 8 hr, the reaction mixture is cooled and filtered. The filtrate is neutralized with 1 M NaOH. The aqueous layer is extracted with EtOAc (300 mL). The organics are dried (Na2SO4), filtered and concentrated in vacuo. The crude product is chromatographed on silica gel, eluting with CH2Cl2 to afford the title compound (0.90 g, 43%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 8 hr
  3. temperaturethe reaction mixture is cooled
  4. filtrationfiltered
  5. extractionThe aqueous layer is extracted with EtOAc (300 mL)
  6. dry with materialThe organics are dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product is chromatographed on silica gel
  10. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-d567173a966040fe8fce61a1b01b4a96
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Reaction notes

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