Water → Thiazole, 2-bromo-4-(3-methylphenyl)-

HRID 2263303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263303
[BrH:1].C(O)(=O)C.[CH3:6][C:7]1[CH:8]=[C:9]([C:13](=O)[CH2:14][S:15][C:16]#[N:17])[CH:10]=[CH:11][CH:12]=1.O>C(O)(=O)C>[Br:1][C:16]1[S:15][CH:14]=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH3:6])[CH:8]=2)[N:17]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 862450512-(3-Methylphenyl)-2-oxoethyl thiocyanate

Produkt 1

HCID 49758214Thiazole, 2-bromo-4-(3-methylphenyl)-Ausbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A 25% hydrogen bromide/acetic acid (20 ml) solution was added to a solution of 2-(3-methylphenyl)-2-oxoethyl thiocyanate (2.29 g, 12.0 mmol) in acetic acid (20 ml), and the mixture was stirred at 130° C. for 2 hours. Water was poured to the reaction mixture, 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 2.03 g (66.8%) of the desired product 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-406f9e775fb441d9957df316f39d8671
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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