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

HRID 1297165Notes

Reaction equation

HRID 1297165 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-3771c17222ef4a6e95c0cd089d0be730
Source dataset
uspto-grants-2007_07
Patent number
US07250430B2

Reaction notes

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