Sodium Cyanide → HCID 22063940, compound

HRID 1828190Notes

Reaction equation

HRID 1828190 reaction equation
Cl[CH2:2][C:3]1[CH:17]=[CH:16][C:6]2[N:7]([CH:12]3[CH2:15][CH2:14][CH2:13]3)[C:8](=[O:11])[N:9]([CH3:10])[C:5]=2[CH:4]=1.[C-:18]#[N:19].[Na+]>CS(C)=O.O>[CH:12]1([N:7]2[C:6]3[CH:16]=[CH:17][C:3]([CH2:2][C:18]#[N:19])=[CH:4][C:5]=3[N:9]([CH3:10])[C:8]2=[O:11])[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 17952495HCID 17952495, compound

Product 1

HCID 22063940HCID 22063940, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-Chloromethyl-1-cyclobutyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (11.92 g, 47.5 mmol) in methyl sulfoxide (50 mL) was added sodium cyanide (6.6 g). The reaction was heated to 90° C. for 2 hours then was cooled, diluted with water and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give (1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-acetonitrile (11.5 g).

Workup

  1. temperaturethen was cooled
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81a0a25698b247749edde03a73769a16
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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