Sodium hydride → Diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1h-imidazol-5-yl]-2-benzylmalonate

HRID 2257207

Reaktionsgleichung

Reaktionsgleichung von HRID 2257207
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].Cl.[CH2:22]([C:26]1[N:27]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:28](CCl)=[CH:29][N:30]=1)[CH2:23][CH2:24][CH3:25]>CN(C)C=O>[CH2:22]([C:26]1[N:27]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:28]([C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:6]([O:5][CH2:4][CH3:3])=[O:7])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:29][N:30]=1)[CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 69090Diethyl 2-benzylpropanedioateHCID 193515432-n-butyl-1-(2-chlorophenyl)methyl-5chloromethyl-1H-imidazole hydrochloride

Produkt 1

HCID 57500985Diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1h-imidazol-5-yl]-2-benzylmalonateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To dry dimethylformamide (50 mL) under argon was added sodium hydride (0.53 g, 0.022 mol) followed by diethyl benzyl malonate (5.51 g, 0.022 mol) in dimethylformamide (10 mL) at 0° C. The mixture was stirred at ambient temperature for one hour. A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-chloromethyl-1H-imidazole hydrochloride (3.5 g, 0.0105 mol) in dimethylformamide (40 mL) was added over 5 minutes. The reaction mixture was stirred at 25° C. for 18 hours, then partitioned between water and methylene chloride. The organic layer was washed with water, dried, and concentrated. The crude product was flash chromatographed over silica gel to give 4.54 g (85%) of the title compound as an oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 25° C. for 18 hours
  2. custompartitioned between water and methylene chloride
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-767df955b6cd445ea54836626908ce60
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656650

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