Malononitrile → 2-(1-Ethoxypropylidene)malononitrile

HRID 2192203Notes

Reaction equation

HRID 2192203 reaction equation
[CH2:1]([C:4]#[N:5])[C:2]#[N:3].[C:6](OCC)(OCC)([O:9][CH2:10][CH3:11])[CH2:7][CH3:8]>C(O)C>[CH2:10]([O:9][C:6](=[C:1]([C:4]#[N:5])[C:2]#[N:3])[CH2:7][CH3:8])[CH3:11]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 66995Ethyl orthopropionate

Product 1

HCID 2314702-(1-Ethoxypropylidene)malononitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33.03 g (0.5 mol) of malonodinitrile and 88.13 g (99.02 ml, 0.5 mol) of triethyl orthopropionate are heated at 100° C. for two hours, and the ethanol which is formed during this is distilled off overhead. The reaction mixture is left to cool and added to ca. 500 ml of water. The aqueous phase is extracted with ethyl acetate, then the organic phase is dried with sodium sulfate and, after filtering off the drying agent, is concentrated by evaporation. The resulting 72 g (purity ca. 90%) of (1-ethoxy-propylidene)malononitrile are used in the subsequent step without further purification.

Workup

  1. distillationthis is distilled off overhead
  2. waitThe reaction mixture is left
  3. temperatureto cool
  4. additionadded to ca. 500 ml of water
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. dry with materialthe organic phase is dried with sodium sulfate
  7. filtrationafter filtering off the drying agent
  8. concentrationis concentrated by evaporation
  9. customThe resulting 72 g (purity ca. 90%) of (1-ethoxy-propylidene)malononitrile are used in the subsequent step without further purification

Sources & evidence

ORD record
ord-43df4655fc124e52a6dfeabc4d52d02f
Source dataset
uspto-grants-2012_12
Patent number
US08329717B2

Reaction notes

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