Sodium Hydroxide → HCID 22019492, compound

HRID 6966Notes

Reaction equation

HRID 6966 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])[S:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.[OH-].[Na+]>C(Cl)(Cl)Cl.CC(O)=O>[Br:12][C:7]1[S:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:2][CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 220194954-Methylsulfanylthiophene-2-sulfonamide

Product 1

HCID 22019492HCID 22019492, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-methylsulfanylthiophene-2-sulfonamide (210 mg, 1.00 mmol) in CHCl3 (10 mL) and AcOH (10 mL) is added N-bromosuccinimide (231 mg, 1.30 mmol). The reaction mixture is stirred at room temperature for 7 hr. After 7 hr, the reaction mixture is neutralized with 1 M NaOH and the solution is extracted with EtOAc (200 mL). The organic layer is washed with brine then dried (Na2SO4), filtered and concentrated in vacuo. The crude product is chromatographed on silica gel, eluting with Hex:EtOAc (3:1) to afford the title compound (200 mg, 70%).

Workup

  1. waitAfter 7 hr
  2. extractionthe solution is extracted with EtOAc (200 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is chromatographed on silica gel
  8. washeluting with Hex

Sources & evidence

ORD record
ord-0942076c4c394968b6a28abbf66cf3d6
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Reaction notes

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