Malononitrile → 1,1-Dicyanocyclopentane

HRID 1607616

Reaction equation

HRID 1607616 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.[C:7](#[N:11])[CH2:8][C:9]#[N:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:8]1([C:7]#[N:11])([C:9]#[N:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 80561,4-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 151720351,1-DicyanocyclopentaneYield 53.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 43.19 g of 1,4-dibromobutane, 13.2 g of malononitrile, 55.3 g of potassium carbonate and 1 liter of acetonitrile was refluxed for 42 hours, filtered while hot and evaporated to dryness giving a dark oil. This oil was vacuum distilled, giving 12.8 g 1,1-cyclopentanedicarbonitrile.

Workup

  1. temperaturewas refluxed for 42 hours
  2. filtrationfiltered while hot and
  3. customevaporated to dryness
  4. customgiving a dark oil
  5. distillationdistilled

Sources & evidence

ORD record
ord-5634bc3ff060447d8c4c4a535b857e90
Source dataset
uspto-grants-1989_09
Patent number
US04866092

Linked notes

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