Hydrochloric Acid → 1-Propene-1,1,3-tricarbonitrile, 2-phenyl-

HRID 1377414Notes

Reaction equation

HRID 1377414 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](#[N:16])[CH2:13][C:14]#[N:15].C([O-])(=O)C.[NH4+].Cl>C(O)C.O>[C:2]1([C:1]([CH2:9][C:10]#[N:11])=[C:13]([C:12]#[N:16])[C:14]#[N:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 64799BenzoylacetonitrileHCID 517165Ammonium Acetate

Product 1

HCID 46214401-Propene-1,1,3-tricarbonitrile, 2-phenyl-Yield 61.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 250 grams (1722 mmol, 1 eq) of benzoylacetonitrile, 284 grams (270 mL, 4306 mmol, 2.5 eq) of malononitrile and 138 grams (1784 mmol, 1.04 eq) of ammonium acetate in 2500 mL of ethanol was heated to reflux for 1.5 hours and then cooled to room temperature. To this mixture was added 190 mL of 12M hydrochloric acid dropwise with cooling (ice/water bath). The mixture was placed in a separate flask and a solid formed and filled the flask. To this mixture was added 3300 mL of water with stirring. The solid was collected and washed with 2 liters of water and triturated with 1200 mL of ethanol to give 203.3 grams (61% yield) of pure 2-phenyl-1,1,3-tricyanopropylene, mp 105°-107° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. customThe mixture was placed in a separate flask
  4. customa solid formed
  5. additionfilled the flask
  6. customThe solid was collected
  7. washwashed with 2 liters of water
  8. customtriturated with 1200 mL of ethanol

Sources & evidence

ORD record
ord-dffdf0d6100d4cabb5e02c2eddb0d80b
Source dataset
uspto-grants-1997_09
Patent number
US05665522

Reaction notes

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