Water → 4-Cyanomethyl-1-(2-propyl)imidazole

HRID 865087Notes

Reaction equation

HRID 865087 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)#[N:4].[CH3:11][CH:12](I)[CH3:13].O>CN(C)C=O.C(Cl)(Cl)Cl>[C:3]([CH2:5][C:6]1[N:7]=[CH:8][N:9]([CH:12]([CH3:13])[CH3:11])[CH:10]=1)#[N:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178510863HCID 178510863, compound

Product 1

HCID 207459354-Cyanomethyl-1-(2-propyl)imidazole

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

450 mg of sodium hydride (60%) was added to 5 ml of dimethylformamide, and a solution of 1.0 g of 4-cyanomethylimidazole in 10 ml of dimethylformamide was added dropwise to the resulting suspension. After 1 hour of stirring at room temperature, 0.94 ml of 2-propyl iodide was added to the resulting solution and stirred at room temperature for 2 hours. To the reaction solution was added water and chloroform, and the resulting organic layer was collected and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue was subjected to silica gel column chromatography eluted with chloroform-methanol (30:1) to obtain 500 mg of 4-cyanomethyl-1-(2-propyl)imidazole.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. customthe resulting organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfollowed by evaporation of the solvent
  5. washeluted with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-ceea582fecea4da39737b741231fa1c4
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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