Ethanol → 1-Propene-1,1,3-tricarbonitrile, 2-phenyl-

HRID 893565Notes

Reaction equation

HRID 893565 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+].C(O)C>O.Cl>[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 702EthanolHCID 8010MalononitrileHCID 64799BenzoylacetonitrileHCID 517165Ammonium Acetate

Product 1

HCID 46214401-Propene-1,1,3-tricarbonitrile, 2-phenyl-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of benzoylacetonitrile (9.94 g, 0.0685 mole), malononitrile (11.3 g, 0.17 mole), ammonium acetate (5.4 g, 0.07 mole) and ethanol (100 mL) was heated at reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was diluted with water (50 mL) and concentrated hydrochloric acid (7.5 mL) was added dropwise over 5 minutes. The resulting precipitate was collected by filtration and washed with water and ligroin. The yield was 10.0 g (76%), m.p. 92°-98° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. additionwas added dropwise over 5 minutes
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water and ligroin

Sources & evidence

ORD record
ord-1d7d351ed5754d7cb138690bf15bdb9f
Source dataset
uspto-grants-1992_06
Patent number
US05126311

Reaction notes

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