Tetracyanoethylene → (2-Chloroethoxy)-(6-chloropyridin-3-yl)acetonitrile
Reaction equation
C[Si]([C:5]#[N:6])(C)C.C(C(C#N)=C(C#N)C#N)#N.ClCCO[CH:21]([O:29][CH2:30][CH2:31][Cl:32])[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[N:26][CH:27]=1>C(#N)C>[Cl:32][CH2:31][CH2:30][O:29][CH:21]([C:22]1[CH:27]=[N:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:5]#[N:6]Participants
Procedure
Trimethylsilyl cyanide (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 was 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
- temperaturethe reaction solution was heated
- temperatureunder reflux for five hours
- waitThe reaction solution was left
- customthe solvent was evaporated under reduced pressure
- additionEthyl acetate was added to the resulting residue
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=8:1)
Sources & evidence
- ORD record
- ord-7bd8a018904f4685a7274b8784753a51
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973033B2
Reaction notes
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