Water → HCID 21098653, compound

HRID 1351291Notes

Reaction equation

HRID 1351291 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[S:7][C:8]([Br:11])=[CH:9][CH:10]=1)(=[O:5])=[O:4].[H-].[Na+].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:17].O>O1CCCC1.C(OCC)(=O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH2:15][N:2]([CH3:1])[S:3]([C:6]2[S:7][C:8]([Br:11])=[CH:9][CH:10]=2)(=[O:4])=[O:5])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 15203645-BroMo-thiophene-2-sulfonic acid M ethylaMide

Product 1

HCID 21098653HCID 21098653, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromothiophene-2-sulfonic acid methyl-amide (608 mg) in tetrahydrofuran (5 mL) was added 60% sodium hydride (115 mg). After stirring for 20 minutes, 2-bromo-1-(4-fluorophenyl)ethanone (630 mg) was added. After adding water and ethyl acetate, and washing the organic layer with saturated sodium chloride water, this solution was dried with anhydrous sodium sulfate. The residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate) and the title compound (464 mg) was obtained as a yellow oily substance.

Workup

  1. washwashing the organic layer with saturated sodium chloride water
  2. dry with materialthis solution was dried with anhydrous sodium sulfate
  3. customThe residue that was obtained
  4. customupon removing the solvent
  5. customby evaporation
  6. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2bb6a6d508844cbfbfc84d6e1733606f
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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