Malononitrile → HCID 19010195, compound

HRID 1741558Notes

Reaction equation

HRID 1741558 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].I[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1>C(#N)C>[C:5]([CH:4]([C:3]#[N:7])[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)#[N:6]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 966574-Iodobenzaldehyde

Product 1

HCID 19010195HCID 19010195, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a 0.10 formula weight of sodium hydride suspended in 1 L acetonitrile in an atmosphere of dry argon is added 0.11 mole malononitrile dissolved in 0.10 L acetonitrile while adequate external cooling is applied to maintain the temperature of the reaction mixture in the range 0° C. to 10° C. To this mixture 0.05 formula weight of 4-iodobenzaldehyde is added followed by a solution of 0,005 formula weight of tetrakis(triphenylphosphene)palladium[0] in 0.50L argon-saturated acetonitrile. The resulting mixture is refluxed under argon with rapid stirring for 66 hours. The resulting mixture is concentrated in vacuo to a volume of 100 ml and the resulting mixture is treated with 500 ml ethyl ether. The salt which precipitated is removed by filtration and, while not with ether, suspended in 0.5 L water. The resulting suspension is acidified to pH=1.0 with concentrated hydrochloric acid to precipitate the 4-(dicyanomethyl)benzaldehyde.

Workup

  1. temperatureexternal cooling
  2. temperatureto maintain the temperature of the reaction mixture in the range 0° C. to 10° C
  3. temperatureThe resulting mixture is refluxed under argon
  4. concentrationThe resulting mixture is concentrated in vacuo to a volume of 100 ml
  5. additionthe resulting mixture is treated with 500 ml ethyl ether
  6. customThe salt which precipitated
  7. customis removed by filtration
  8. customto precipitate the 4-(dicyanomethyl)benzaldehyde

Sources & evidence

ORD record
ord-d3ed50a07fd74f539e04b24e2b0b4b19
Source dataset
uspto-grants-1994_08
Patent number
US05334333

Reaction notes

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