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

HRID 257717Notes

Reaction equation

HRID 257717 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-88a687fee7d1467c8682d480baad5d94
Source dataset
uspto-grants-1993_11
Patent number
US05264320

Reaction notes

Loading…