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Potassium Carbonate → HCID 19973443, Verbindung

HRID 1452044
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1452044
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([CH3:17])[N:16]=2)[CH:13]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.ClC1C=CC=C(C(OO)=O)C=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([CH3:17])[N:16]=2)[CH:13]=1)=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 19973464HCID 19973464, Verbindung

Produkt 1

HCID 19973443HCID 19973443, VerbindungAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70297
m-Chloroperbenzoic acid
Katalysator
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4.95 g of the 6-((4-chlorobutyl)thiomethyl)-2methylimidazo[1,2-a]pyridine prepared in the Preparative Example 17 was dissolved in 50 ml of dichloromethane, followed by the cooling of the obtained solution with ice. A solution of 3.18 g of m-chloroperbenzoic acid in 20 ml of dichloromethane was dropped into the resulting solution in 20 minutes. After one hour, 0.16 g of m-chloroperbenzoic acid was further added to the obtained mixture. The obtained mixture was additionally stirred for 30 minutes, followed by the addition of an aqueous solution of sodium thiosulfate. The obtained mixture was vigorously stirred at room temperature for 15 minutes, followed by the addition of an aqueous solution of potassium carbonate. The obtained mixture was extracted with dichloromethane. The organic phase was dried over anhydrous potassium carbonate and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1 to 30:1)] to give 4.18 g of the title compound as a pale-pink solid (yield: 79%).

Aufarbeitung

  1. temperaturecooling of the obtained solution with ice
  2. stirringThe obtained mixture was vigorously stirred at room temperature for 15 minutes
  3. extractionThe obtained mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over anhydrous potassium carbonate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1 to 30:1)]

Quellen und Nachweise

ORD-Eintrag
ord-e54eb8c93be8469f9a259bbc3c5f4802
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05606061

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