Sodium Hydroxide → 2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile

HRID 552822Notes

Reaction equation

HRID 552822 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].C1N=CN([C:16](N2C=NC=C2)=[O:17])C=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[O:17]=[C:16]1[NH:10][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[NH:1]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 116439742-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrileYield 101.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 3,4-diaminobenzonitrile (350 mg) in toluene (5.5 ml) was added CDI (554 mg), followed by stirring at 125° C. for 2 hours. To the reaction mixture was added a 1M aqueous NaOH solution (0.117 ml), followed by extraction with EtOAc. The organic layer was dried over anhydrous MgsO4, and then filtered, and the filtrate was concentrated. It was powdered/washed with IPE/IPA to obtain 2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile (423 mg) as colorless powders.

Workup

  1. extractionfollowed by extraction with EtOAc
  2. customThe organic layer was dried over anhydrous MgsO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. washIt was powdered/washed with IPE/IPA

Sources & evidence

ORD record
ord-c7116d9142f2408989c14c2128d4b316
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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