4-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one → 7-(1-Ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carbonitrile

HRID 1698587Notes

Reaction equation

HRID 1698587 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[C:5]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:4][CH:3]=1.[Cu](C#N)[C:19]#[N:20]>CN1CCCC1=O.C(=O)(O)[O-].[Na+]>[CH2:14]([CH:13]([C:5]1[C:6]2[N:7]([CH3:12])[C:8](=[O:11])[NH:9][C:10]=2[C:2]([C:19]#[N:20])=[CH:3][CH:4]=1)[CH2:16][CH3:17])[CH3:15]

Participants

5

Reactant 2

HCID 672727554-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneHCID 178418260HCID 178418260, compound

Product 1

HCID 672726697-(1-Ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carbonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (300 mg, 1.01 mmol) and copper cyanide (116 mg, 1.30 mmol) in 1-methyl-2-pyrrolidone (3 mL) was irradiated by microwave (200 w) at 150° C. for 1 h. After cooling, to the reaction mixture was diluted with saturated sodium bicarbonate, and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was washed with 50% diisopropyl ether/n-hexane to give the title compound (209 mg, 86%).

Workup

  1. customwas irradiated by microwave (200 w) at 150° C. for 1 h
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with 50% diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-f640696bbf26427f998a576e9bf0f33a
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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