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m-Chloroperbenzoic acid → HCID 57736422, Verbindung

HRID 1641679
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641679
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
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Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 57736477HCID 57736477, Verbindung

Produkt 1

HCID 57736422HCID 57736422, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-84547195edea440a92937beeeef84fd0
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114886B2

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