Tetracyanoethylene → (2-Chloroethoxy)-(6-chloropyridin-3-yl)acetonitrile

HRID 2235772Notes

Reaction equation

HRID 2235772 reaction equation
[C:1](C(C#N)=C(C#N)C#N)#[N:2].ClCCO[CH:15]([O:23][CH2:24][CH2:25][Cl:26])[C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[N:20][CH:21]=1>C(#N)C>[Cl:26][CH2:25][CH2:24][O:23][CH:15]([C:16]1[CH:21]=[N:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:1]#[N:2]

Participants

4

Reactant 2

HCID 12635TetracyanoethyleneHCID 866151495-[Bis-(2-chloroethoxy)methyl]-2-chloropyridine

Product 1

HCID 86615148(2-Chloroethoxy)-(6-chloropyridin-3-yl)acetonitrileYield 471.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl cyamide (1.88 mL) and tetracyanoethylene (240 mg) were added to a solution of 5-[bis-(2-chloroethoxy)methyl]-2-chloropyridine (2.67 g) in acetonitrile (50 mL), and the reaction solution was heated under reflux for five hours. The reaction solution was left to cool to room temperature, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the resulting residue. The organic layer washed with brine and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=8:1) to obtain 2.04 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for five hours
  3. waitThe reaction solution was left
  4. customthe solvent was evaporated under reduced pressure
  5. additionEthyl acetate was added to the resulting residue
  6. washThe organic layer washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-1d7a8980eed543c98bb646d236348756
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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