Sodium hydride → 2-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole

HRID 6482

Reaktionsgleichung

Reaktionsgleichung von HRID 6482
[CH2:1]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:14]=1[CH2:15]Cl>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:15][C:14]2[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:13]=2[Cl:12])[CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 118153512-butyl-1H-imidazole

Produkt 1

HCID 199367742-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazoleAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 2 n-butylimidazole (3.75 g, 0.03 mol) in dry dimethylformamide (4 ml) was added to sodium hydride (0.95 g) in dimethylformamide (18 ml). After the gas evolution subsided, the mixture was stirred one hour under argon and 2-chloro-6-fluorobenzylchloride (5.5 q, 0.031 mol) in dimethylformamide (7 ml) was added slowly. The mixture was stirred for 17 hours at ambient temperature, diluted with ice water and extracted with ethyl acetate. The washed, dried, concentrated organic layer provided 7.63 g (94%) of 2-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole whose NMR was consistent with the structure. This material was used without further purification.

Aufarbeitung

  1. stirringThe mixture was stirred for 17 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. customThe washed, dried

Quellen und Nachweise

ORD-Eintrag
ord-bc86844699a84905a340fdf779a0e7ca
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248689

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