Tetrahydrofuran → 4-(2-bromo-acetyl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

HRID 1434683Notes

Reaction equation

HRID 1434683 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br-:19].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C1[CH2:44][O:43][CH2:42]C1>O>[Br:19][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:42][O:43][CH3:44])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 210825294-Acetyl-n-(thiazol-2-yl)benzenesulfonamideHCID 21124087Pyridiniumtribromide

Product 1

HCID 866116974-(2-bromo-acetyl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-acetyl-N-thiazol-2-yl-benzenesulfonamide (10 mmol) in THF (50 mL) was added pyridinium tribromide (10 mmol), and the mixture was stirred for 4 h. The reaction mixture was diluted with water (30 mL) and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 4-(2-bromo-acetyl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (8.2 mmol) as a white solid.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-182a8cebbf694424bd1e4f6844073fed
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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