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Sodium Chloride → 4-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

HRID 265061
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 265061
[H-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH3:16])[NH:9][C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:20]=1.[Cl-].[Na+]>CN(C)C(=O)C>[C:3]([C:6]1[N:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH3:16])[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:21][CH:20]=2)[C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4]
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Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441657HCID 178441657, Verbindung

Produkt 1

HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazoleAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

0.192 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to a solution of 0.843 g of 4-acetyl-2-butylimidazole-5-carbonitrile [prepared as described in Preparation 24(i)] in 17 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 20 minutes. 1.68 g of t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate was then added, and the resulting mixture was stirred at 55° C. for 2.5 hours. At the end of this time, an aqueous solution of sodium chloride was added to the mixture, which was then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting oily residue was purified by column chromatography through silica gel, using 4:1 and 2:1 by volume mixtures of hexane and ethyl acetate as the eluent, to afford 1.14 g of the title compound as a viscous oil.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 55° C. for 2.5 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting oily residue was purified by column chromatography through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ae9759cfac2b4ec8b02a96f156c4c4e1
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05646171

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