m-Chloroperbenzoic acid → HCID 57736422, compound

HRID 1641679Notes

Reaction equation

HRID 1641679 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:21]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])[C:22]2[C:23]([CH3:31])=[CH:24][C:25]([C:28]([NH2:30])=[O:29])=[N:26][CH:27]=2)=[O:20])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:21]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])[C:22]2[C:23]([CH3:31])=[CH:24][C:25]([C:28]([NH2:30])=[O:29])=[N:26][CH:27]=2)(=[O:9])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57736477HCID 57736477, compound

Product 1

HCID 57736422HCID 57736422, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (66 mg, 0.25 mmol) was added to a solution of 5-[[(4-chlorophenyl)sulfinyl](2,5-difluorophenyl)methyl]-4-methylpyridine-2-carboxamide (105 mg, 0.25 mmol) in methylene chloride (5 ml) at 0° C. After stirring for 5 days at room temperature, the reaction mixture was washed with 1 N aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to preparative thin-layer chromatography (developed with methylene chloride:methanol=40:1, and eluted with methylene chloride:methanol=4:1). The obtained fraction was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether and collected by filtration, thus to obtain the title compound (56 mg, 0.13 mmol, 51%) as a white solid.

Workup

  1. washthe reaction mixture was washed with 1 N aqueous sodium hydroxide
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washthin-layer chromatography (developed with methylene chloride:methanol=40:1, and eluted with methylene chloride:methanol=4:1)
  6. concentrationThe obtained fraction was concentrated under reduced pressure
  7. washthe resulting residue was washed with a mixed solvent of ethanol and diethyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-84547195edea440a92937beeeef84fd0
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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