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Potassium Carbonate → 4-[4-(4-Fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzamidoxime

HRID 2257390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2257390
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Cl.[NH2:34][OH:35]>CCO.O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1](=[N:34][OH:35])[NH2:2])=[CH:8][CH:7]=3)[NH:10][C:11]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:15][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 154078722-(4-cyanophenyl)4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole

Produkt 1

HCID 1361462794-[4-(4-Fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzamidoximeAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a mixture of 2-(4-cyanophenyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole (3.0 g, 8.7 mmol) [See Ex. 1 above] and K2CO3 (2.4 g, 17 mmol) in EtOH (120 mL) and H2O (6 mL) was added hydroxylamine hydrochloride (1.2 g, 17 mmol). After heating at reflux for 24 h, the reaction mixture was poured into H2O. The precipitate was collected, washed with H2O and air-dried. The crude product was dissolved in acetone, silica gel was added and the solvent was evaporated. The impregnated silica gel was added to the top of a flash column and the column was eluted with a solvent gradient of 2-10% MeOH/CHCl3 to afford the title compound as a white solid (3.0 g, 91%): ESMS (m/z): 374 (M+ +H).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for 24 h
  3. customThe precipitate was collected
  4. washwashed with H2O
  5. customair-dried
  6. dissolutionThe crude product was dissolved in acetone
  7. additionsilica gel was added
  8. customthe solvent was evaporated
  9. additionThe impregnated silica gel was added to the top of a flash column
  10. washthe column was eluted with a solvent gradient of 2-10% MeOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-af935e2be51c47bda76b963dfac09c1e
Quelldatensatz
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05656644

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