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

HRID 234752Notes

Reaction equation

HRID 234752 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 (1.722 mol, 1 eq) of benzoylacetonitrile, 284 grams (270 mL, 4.306 mol, 2.5 eq) of malononitrile and 138 grams (1.784 mol, 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. To this mixture was added 3300 mL of water with stirring. The solid was collected and washed with 2 liters of water and stirred with 1200 mL of ethanol to give 203.3 grams (61% yield) of product.

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. customThe solid was collected
  6. washwashed with 2 liters of water
  7. stirringstirred with 1200 mL of ethanol

Sources & evidence

ORD record
ord-b35a7e097b4e48569570bf8c59f094d6
Source dataset
uspto-grants-1997_01
Patent number
US05596025

Reaction notes

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