4-Bromophenacyl bromide → 4-(4-Bromophenyl)-2-methyl-1,3-thiazole

HRID 497222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497222
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=O.[C:12]([NH2:15])(=[S:14])[CH3:13].[OH-].[Na+]>O1CCOCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:15]=[C:12]([CH3:13])[S:14][CH:2]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 74544-Bromophenacyl bromideHCID 14798Sodium HydroxideHCID 2723949Thioacetamide

Produkt 1

HCID 6201384-(4-Bromophenyl)-2-methyl-1,3-thiazoleAusbeute 103,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,4′-dibromoacetophenone (5 g, 18 mmol) in dioxane (180 ml) was added thioacetamide (6.76 g, 90 mmol), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, and made basic by addition of 2N NaOH aqueous solution. The whole was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (4.73 g, 99% yield).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. extractionThe whole was extracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-d83fc27440404fcfa6d59654903c1ce6
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949536B2

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