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Benzoyl chloride → 7-Benzoylimidazo[5,1-b]thiazole

HRID 1839298
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1839298
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[S:14]1[CH:18]=[CH:17][N:16]2[CH:19]=[N:20][CH:21]=[C:15]12.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(=S)=S.ClCCl>[C:5]([C:21]1[N:20]=[CH:19][N:16]2[CH:17]=[CH:18][S:14][C:15]=12)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 6451240Aluminum(III) ChlorideHCID 21262404Imidazo[5,1-b]thiazole

Produkt 1

HCID 226320567-Benzoylimidazo[5,1-b]thiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

Aluminum chloride (5.33 g) was added to a solution of 4.64 ml of benzoyl chloride in 50 ml of carbon disulfide. A solution of 1.24 g of imidazo[5,1-b]thiazole in 50 ml of dichloromethane was added dropwise thereto. The mixture was stirred at room temperature for 2 hr. The reaction solution was poured into 50 g of ice. Dichloromethane (100 ml) was added thereto. Sodium carbonate (16.7 g) and 16.7 g of sodium sulfate were added in that order to the mixture with stirring. The insolubles were removed by filtration through Celite, and then washed with dichloromethane. Filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to dichloromethane:ethyl acetate=2:1) to give 1.39 g of 7-benzoylimidazo[5,1-b]thiazole.

Aufarbeitung

  1. stirringwith stirring
  2. customThe insolubles were removed by filtration through Celite
  3. washwashed with dichloromethane
  4. concentrationFiltrate was concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to dichloromethane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5173fe91ebe141afba62b46513914ac4
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06677331B2

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