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

HRID 1634023

Reaction equation

HRID 1634023 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6ce79da2204742599c88902fe82d6331
Source dataset
uspto-grants-2003_01
Patent number
US06506738B1

Linked notes

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