Water → 2-Bromo-5-ethyl-4-phenyl-1,3-thiazole

HRID 2263197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263197
[CH2:1]([CH:3]([S:12][C:13]#[N:14])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=C)[CH3:2].[BrH:15].C(O)(=O)C.O>C(O)(=O)C>[Br:15][C:13]1[S:12][C:3]([CH2:1][CH3:2])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:14]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 862451611-Ethyl-2-phenylprop-2-en-1-yl thiocyanate

Produkt 1

HCID 687783792-Bromo-5-ethyl-4-phenyl-1,3-thiazoleAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 1-ethyl-2-phenylprop-2-en-1-yl thiocyanate (4.15 g, 20.2 mmol) in acetic acid (40 ml) was added a 25% hydrogen bromide/acetic acid (40 ml) solution, and the mixture was stirred at 130° C. for 2 hours. Water was poured into the reaction solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the desired product (4.02 g, 74.2%) as an oil.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-c88dff46ed624628b4738a2a32025952
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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