Aniline → 2H-Benzimidazol-2-one, 1,3-dihydro-1-phenyl-

HRID 1634023

Reaktionsgleichung

Reaktionsgleichung von HRID 1634023
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18]([O-])([O-])=[O:19].[K+].[K+]>CC#N>[C:3]1([N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:18]2=[O:19])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Produkt 1

HCID 846572H-Benzimidazol-2-one, 1,3-dihydro-1-phenyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-fluoronitrobenzene was treated with aniline in the prescence of K2CO3 in CH3CN and heated to reflux for 12 h. The solution is cooled, filtered and the solvent removed. The nitro group is reduced with catalytic hydrogenation and the diamine treated with CDI to give 1-phenyl-1,3-dihydro-benzoimidazol-2-one.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. temperatureThe solution is cooled
  4. filtrationfiltered
  5. customthe solvent removed
  6. additionthe diamine treated with CDI

Quellen und Nachweise

ORD-Eintrag
ord-6ce79da2204742599c88902fe82d6331
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506738B1

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