Sodium Carbonate → 2-(2-Thienyl)thiazole

HRID 1625913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625913
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 27339602-Thiopheneboronic acid

Produkt 1

HCID 5475102-(2-Thienyl)thiazoleAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Bromothiazole (15.0 g) and 2-thiopheneboronic acid (14.0 g) were dissolved in dimethoxyethane (150 ml). To the mixture was added bis(triphenyl)phosphine palladium(II)dichloride (3.2 g) and 2M sodium carbonate (137 ml), and the mixture was refluxed under argon atmosphere for 2 hours. The mixture was cooled to room temperature, and the reaction solution was diluted with ethyl acetate, and washed with water. The organic layer was collected, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=96:4) to give 2-(2-thienyl)thiazole (9.87 g) as oil. APCI-Mass m/z 168 (M+H)

Aufarbeitung

  1. temperaturethe mixture was refluxed under argon atmosphere for 2 hours
  2. washwashed with water
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=96:4)

Quellen und Nachweise

ORD-Eintrag
ord-02ac42cd92ec4fcdba6c346cd1381a01
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785403B2

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