Potassium Cyanide → {6-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-yl]-3-pyridinyl}acetonitrile

HRID 2077776Notes

Reaction equation

HRID 2077776 reaction equation
[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=3)[C:6]=2[CH:20]=1.[C-:25]#[N:26].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[N:13]=[CH:14][C:15]([CH2:18][C:25]#[N:26])=[CH:16][CH:17]=3)[C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 67099483HCID 67099483, compound

Product 1

HCID 67100013{6-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-yl]-3-pyridinyl}acetonitrileYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-1-[5-(chloromethyl)-2-pyridinyl]-2-ethyl-5-(trifluoromethyl)-1H-benzimidazole (from step 5, 550 mg, 1.5 mmol) in DMF (5 ml) and water (1 ml) was added KCN (470 g, 7.2 mmol) at room temperature, and then the reaction mixture was stirred for 2 h. The mixture was diluted with water and extracted with ethyl acetate/toluene (4/1) solution (3×30 ml). The organic layer was washed with water, dried (MgSO4) and concentrated. This was purified by SiO2 column chromatography developing with hexane/ethyl acetate (1/) gave 198 mg (37%) of title compound as orange oil.

Workup

  1. extractionextracted with ethyl acetate/toluene (4/1) solution (3×30 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThis was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-485f7f8d24524c7fa7fc08f42f3cde97
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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