Acetic Acid → HCID 178470172, Verbindung

HRID 241038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241038
[CH:1]1[C:6]([C:7]([CH2:9][NH2:10])=O)=[CH:5][CH:4]=[C:3]([Br:11])[CH:2]=1.Cl.C([O-])(=O)C.[Na+].C(O)(=O)C.[NH:22]=[C:23](SC)[C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:11][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[N:22]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[NH:10][CH:9]=2)=[CH:1][CH:2]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochlorideHCID 10464471ethyl 2-imino-2-(methylthio)acetate

Produkt 1

HCID 178470172HCID 178470172, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 2-amino-4-bromoacetophenone hydrochloride (4.0 g, 16.0 mmol), sodium acetate (6.1 g, 90.0 mmol), acetic acid (4.6 mL, 80.0 mmol) and ethyl 2-imino-2-(methylthio)acetate (7.7 g, 32.0 mmol) in dioxane (40 mL) was stirred at 95° C. overnight. The reaction mixture was carefully neutralized with saturated NaHCO3 solution and extracted with ethyl acetate. The organic solution was dried over sodium sulfate and concentrated. Purification by silica gel column chromatography (ethyl acetate:hexanes 1:1) afforded ethyl 4-(4-bromophenyl)-1H-imidazole-2-carboxylate (3.53 g, 75.0%). MS (EI) for C12H11BrN2O2: 296 (MH+).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (ethyl acetate:hexanes 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-03495ac8991b40ca9c0851dbd5986bf2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

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