Imidazole → methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetate

HRID 12301

Reaktionsgleichung

Reaktionsgleichung von HRID 12301
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.Br[CH:14]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16].O>CN(C=O)C>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH:14]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:15]([O:17][CH3:18])=[O:16])=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 8471TriethylamineHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

Produkt 1

HCID 23092022methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of imidazole (170 mg) and triethylamine (350 ml) in DMF (1 ml), a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (657 mg) in DMF (3 ml) was added. After stirring for an overnight, water was added to the reaction liquid, followed by extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate. The reaction liquid was condensed under reduced pressure and the resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10) to provide methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetate (400 mg) as a yellow oily substance.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe reaction liquid
  5. customcondensed under reduced pressure
  6. customthe resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10)

Quellen und Nachweise

ORD-Eintrag
ord-c5bb6ebc07cd49ad9ab13e25aeb3b07a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727998B2

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