Malononitrile → HCID 86715176, compound

HRID 1529171Notes

Reaction equation

HRID 1529171 reaction equation
Br[C:2]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:14](#[N:18])[CH2:15][C:16]#[N:17].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:16]([CH:15]([C:2]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:14]#[N:18])#[N:17]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 25517Ammonium ChlorideHCID 94944Diethyl bromomethylmalonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86715176HCID 86715176, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

19.156 g (75.686 mmol) of diethyl 2-bromo-2-methylmalonate were initially charged in THF (120 ml), and 5 g (75.686 mmol) of malononitrile and then 8.493 g (75.686 mmol) of potassium tert-butoxide were added. The mixture was then heated to reflux overnight. Ethyl acetate and sat. ammonium chloride solution were then added to the reaction, and the phases were separated. The aqueous phase was extracted two more times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated to dryness. This gave a crude product which was purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted two more times with ethyl acetate
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-df5489a85e2841e0ae1b4693a6ba435c
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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