Water → Butylpropanedinitrile

HRID 2116670Notes

Reaction equation

HRID 2116670 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].I[CH2:13][CH2:14][CH2:15][CH3:16].O>CN(C)C=O>[CH2:13]([CH:2]([C:1]#[N:5])[C:3]#[N:4])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 10962Butyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 12751987ButylpropanedinitrileYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

26.4 g of malononitrile was dissolved in 60 ml of N,N-dimethylformamide and 56 g of potassium carbonate was added thereto, followed by stirring for 1 hour at room temperature. To the solution was added 40 g of iodobutane at about 0° C. and stirred for 30 minutes at the same temperature and for additional 4 hours at room temperature. Then, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give 17 g of 2-butylmalononitrile.

Workup

  1. stirringstirred for 30 minutes at the same temperature and for additional 4 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained

Sources & evidence

ORD record
ord-21eff1cdcb46493c948a4736c1bb2619
Source dataset
uspto-grants-2008_10
Patent number
US07439266B2

Reaction notes

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