Water → HCID 54476889, compound

HRID 865084Notes

Reaction equation

HRID 865084 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)#[N:4].ClCO[CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17].O.CN(C)[CH:23]=[O:24]>C(Cl)(Cl)Cl>[C:3]([CH2:5][C:6]1[NH:7][C:8]([CH2:23][O:24][CH:15]([Si:16]([CH3:17])([CH3:18])[CH3:19])[CH3:14])=[N:9][CH:10]=1)#[N:4]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178510863HCID 178510863, compound

Product 1

HCID 54476889HCID 54476889, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

373 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, to the solution was added 1.9 ml of (2-chloromethoxyethyl)trimethylsilane and stirred at room temperature for 2 hours. The reaction solution was mixed with 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 hexane-ethyl acetate (1:1) to obtain 1.128 g of 4-cyanomethyl-1-trimethylsilylethoxymethylimidazole and 0.362 g of 5-cyanomethyl-1-trimethylsilylethoxymethylimidazole.

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 hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-be63ee2de05a4f5b99adfac2b4ba9498
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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