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Sodium Thiosulfate → 6-chloro-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

HRID 2208992
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2208992
[Cl:1][C:2]1[N:7]=[C:6](SC)[C:5]2[N:10]([CH3:13])[CH:11]=[N:12][C:4]=2[CH:3]=1.[CH:14]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:25][S:26]([O-:29])(=S)=O.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([S:26]([CH3:14])(=[O:29])=[O:25])[C:5]2[N:10]([CH3:13])[CH:11]=[N:12][C:4]=2[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 1178434146-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

Produkt 1

HCID 1178428886-chloro-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.02 (450 mg, 2.11 mmol) in dichloromethane (16 mL) at 0° C., was added mCPBA (≦77%, 972 mg, 4.34 mmol) and mixture was warmed to room temperature. After 80 minutes, an additional 200 mg of mCPBA was added. After an additional twenty minutes, a solution of 50% saturated Na2S2O3 (aq) (20 mL) was added and reaction mixture stirred at room temperature for fifteen minutes. Layers were separated and aqueous was extracted with ethyl acetate (4×15 mL). All organic layers were combined, washed with saturated NaHCO3 (aq) (2×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 6-chloro-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine 2.04.

Aufarbeitung

  1. waitAfter an additional twenty minutes
  2. customreaction mixture
  3. customLayers were separated
  4. extractionaqueous was extracted with ethyl acetate (4×15 mL)
  5. washwashed with saturated NaHCO3 (aq) (2×30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-805407c88c194a49bb78907c01418752
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376441B2

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