m-Chloroperbenzoic acid → HCID 57736477, compound

HRID 1641678Notes

Reaction equation

HRID 1641678 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:20]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[C:21]2[C:22]([CH3:30])=[CH:23][C:24]([C:27]([NH2:29])=[O:28])=[N:25][CH:26]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:20]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[C:21]2[C:22]([CH3:30])=[CH:23][C:24]([C:27]([NH2:29])=[O:28])=[N:25][CH:26]=2)=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57736492HCID 57736492, compound

Product 1

HCID 57736477HCID 57736477, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (259 mg, 0.98 mmol) was added to a solution of 5-[[(4-chlorophenyl)thio](2,5-difluorophenyl)methyl]-4-methylpyridine-2-carboxamide (395 mg, 0.98 mmol) in methylene chloride (10 ml) at 0° C. After stirring for 14 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 flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:1 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 (243 mg, 0.58 mmol, 59%) 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. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=1:1 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-cae7f4619738470d8cbd15a0aa02ff41
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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