Sulfuric acid magnesium salt (1:1) → [4-(2-Methanesulfonylpyrimidin-4-yl)-3-(3-methoxy-5-methylphenyl)-pyrazol-1-yl]acetonitrile

HRID 2390773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390773
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[S:12]([O-:16])([O-])(=O)=[O:13].[Mg+2].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:27]2[C:31]([C:32]3[CH:37]=[CH:36][N:35]=[C:34](SC)[N:33]=3)=[CH:30][N:29]([CH2:40][C:41]#[N:42])[N:28]=2)[CH:23]=[C:24]([CH3:26])[CH:25]=1>ClCCl>[CH3:2][S:12]([C:34]1[N:33]=[C:32]([C:31]2[C:27]([C:22]3[CH:23]=[C:24]([CH3:26])[CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)=[N:28][N:29]([CH2:40][C:41]#[N:42])[CH:30]=2)[CH:37]=[CH:36][N:35]=1)(=[O:16])=[O:13]

Komponenten

5

Edukt 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70297m-Chloroperbenzoic acidHCID 50899518[3-(3-Methoxy-5-methylphenyl)-4-(2-methylthio-pyrimidin-4-yl)pyrazol-1-yl]acetonitrile

Produkt 1

HCID 50899519[4-(2-Methanesulfonylpyrimidin-4-yl)-3-(3-methoxy-5-methylphenyl)-pyrazol-1-yl]acetonitrileAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

m-Chloroperbenzoic acid (4.71 g, 27.3 mmol) and anhydrous magnesium sulfate (6.57 g, 54.6 mmol) in dichloromethane (100 mL) were dissolved at room temperature for 1 hour with stirring. To this solution was added [3-(3-methoxy-5-methylphenyl)-4-(2-methylthio-pyrimidin-4-yl)pyrazol-1-yl]acetonitrile (1.6 g, 4.55 mmol) which was subjected to oxidation to sulfone by stirring for an additional two hours. After completion of the reaction, the precipitate was filtered off and washed with dichloromethane. The filtrate was washed with brine and dichloromethane, and the organic layer was separated, dried over anhydrous magnesium sulfate and concentrated through vacuum distillation. The residue was purified by column chromatography to give the title compound (1.23 g, 70.4%).

Aufarbeitung

  1. stirringby stirring for an additional two hours
  2. customAfter completion of the reaction
  3. filtrationthe precipitate was filtered off
  4. washwashed with dichloromethane
  5. washThe filtrate was washed with brine and dichloromethane
  6. customthe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated through vacuum distillation
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0fe15a6de46e426481ab01a836c9ac2b
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273880B2

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