Ammonium Chloride → [2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl](4-fluorophenyl)-methanone

HRID 1062439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062439
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH:10]=[C:11]([C:13](N(OC)C)=[O:14])[N:12]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][CH:28]=1.[NH4+].[Cl-]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH:10]=[C:11]([C:13]([C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)=[O:14])[N:12]=1

Komponenten

4

Edukt 3

HCID 25517Ammonium ChlorideHCID 222855752-(2-chlorophenyl)-1-(4-chlorophenyl)-N-methoxy-N-methyl-1H-imidazole-4-carboxamideHCID 178418676HCID 178418676, Verbindung

Produkt 1

HCID 22285369[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl](4-fluorophenyl)-methanoneAusbeute 69,5 %

Versuchsvorschrift

To a solution of 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-methoxy-N-methyl-1H-imidazole-4-carboxamide (50.0 mg, 0.133 mmol) in 1.5 mL THE was added a 1.0 M solution of 4-fluorophenylmagnesium bromide (0.27 mL, 0.27 mmol) under argon at rt with stirring. The resultant mixture was stirred for 30 minutes and a saturated aqueous solution of NH4Cl was added. The mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated down in vacuo. The crude product was purified on HPLC to give [2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl](4-fluorophenyl)-methanone as a solid (38.0 mg, 69%): Rf=0.58 (1:1 ethyl acetate/hexanes).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated down in vacuo
  4. customThe crude product was purified on HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d20da7671c5b49fbabc4e10b57719eb5
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960601B2

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