Malononitrile → HCID 14457355, compound

HRID 1587640Notes

Reaction equation

HRID 1587640 reaction equation
[C:1]([CH2:3][C:4]#[N:5])#[N:2].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>O1CCCC1>[C:1]([CH:3]([C:4]#[N:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])#[N:2]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 223913Methyl 11-bromoundecanoate

Product 1

HCID 14457355HCID 14457355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

100 ml of anhydrous tetrahydrofuran are introduced into a three-neck flask with stirrer, reflux condenser and dropping funnel, and 11.22 g (0.10 mol) of potassium tert.butylate are suspended with stirring. 6.61 g (0.10 mol) of 1,1-dicyanomethane dissolved in 20 ml of anhydrous tetrahydrofuran are added dropwise to this, while cooling in ice so that the temperature does not rise above 10° C. Subsequently, 28.0 g (0.10 mol) of methyl 11-bromoundecanoate are added, and the mixture is refluxed for 15 h. After cooling, the precipitated potassium bromide is filtered off, the filtrate is evaporated to dryness in a rotary evaporator, the residue is taken up in 100 ml of diethyl ether, and the solution is washed three times with 50 ml of water each time. The ethereal phase is dried over sodium sulfate and evaporated to dryness in a rotary evaporator, and the resulting crude product is distilled in a short-path distillation apparatus (boiling point 150 to 160° C./0.6 mbar).

Workup

  1. temperaturereflux condenser
  2. additionare added dropwise to this,
  3. temperaturewhile cooling in ice so that the temperature
  4. customdoes not rise above 10° C
  5. temperaturethe mixture is refluxed for 15 h
  6. temperatureAfter cooling
  7. filtrationthe precipitated potassium bromide is filtered off
  8. customthe filtrate is evaporated to dryness in a rotary evaporator
  9. washthe solution is washed three times with 50 ml of water each time
  10. dry with materialThe ethereal phase is dried over sodium sulfate
  11. customevaporated to dryness in a rotary evaporator
  12. distillationthe resulting crude product is distilled in a short-path distillation apparatus (boiling point 150 to 160° C./0.6 mbar)

Sources & evidence

ORD record
ord-a908d0d388e94d428f77f92552363947
Source dataset
uspto-grants-1993_06
Patent number
US05219555

Reaction notes

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