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

HRID 1033887

Reaktionsgleichung

Reaktionsgleichung von HRID 1033887
[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-imidazole

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. g, 0.031 mol) in dimethylformamide (7 mL) was added to produce an exotherm. 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 (94%) of the title compound whose NMR was consistent with the structure. This material was used without further purification.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1a3caf89a12e4a52881d1fd592a780e8
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05312828

Verknüpfte Notizen

Wird geladen…