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Hydrochloric Acid → 1-(2-chlorobenzyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile

HRID 495634
Notes
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Reaction equation

HRID 495634 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[C:3]=1[N:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[C:15](=O)[O:16]CC.[H-].[Na+].Cl>C(O)C>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:14]1[C:3]2[C:4]([C:10]([F:12])([F:11])[F:13])=[CH:5][C:6]([C:8]#[N:9])=[CH:7][C:2]=2[NH:1][C:15]1=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 22327355Ethyl 2-amino-4-cyano-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate

Product 1

HCID 223273581-(2-chlorobenzyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

Ethyl 2-amino-4-cyano-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate (338.7 mg) was dissolved in ethanol (20 ml), and to the solution was added sodium hydride (37.5 mg). The reaction mixture was heated at reflux for 1 hour. After allowing to cool, to the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted 4 times with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (287.0 mg, 96%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool, to the reaction mixture
  4. extractionthe mixture was extracted 4 times with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7c7c7433ec14478b26f241ad4b338f7
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06939887B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes