Malononitrile → [5,5-Dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene] malonitrile

HRID 1283833Notes

Reaction equation

HRID 1283833 reaction equation
Cl([O-])(=O)(=O)=[O:2].Cl[C:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9](=[N+:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:8]=1.[C:20](#[N:24])[CH2:21][C:22]#N.C([N:27]([CH2:30]C)CC)C>C(O)C>[CH3:13][C:11]1([CH3:14])[CH2:10][C:9]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][C:7](=[C:22]([C:30]#[N:27])[CH:21]([OH:2])[C:20]#[N:24])[CH2:12]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 21516721N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate

Product 1

HCID 54020833[5,5-Dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene] malonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidiniumperchlorate (9.4 g., 0.03 mol.) and malononitrile (2.0 g., 0.03 mol.) are dissolved in warm ethanol (25 ml.). Triethylamine (4.6 ml.) is then added and a vigorous reaction takes place with a solid precipitating. The mixture is then heated at reflux for 5 minutes. After chilling, the crude dye is collected on a filter and rinsed with ethanol and dried. After one recrystallization from methanol, the yield of purified dye is 3.0 g. (83%), m.p. 246°-247°C. This purified dye is an excellent light-absorbing dye in photographic layers as shown in the absorption data in Table 1 hereinafter.

Workup

  1. customa vigorous reaction
  2. customprecipitating
  3. temperatureThe mixture is then heated
  4. temperatureat reflux for 5 minutes
  5. temperatureAfter chilling
  6. customthe crude dye is collected on
  7. filtrationa filter
  8. washrinsed with ethanol
  9. customdried
  10. customAfter one recrystallization from methanol

Sources & evidence

ORD record
ord-16751484f94b4a7397f1e90899d2f1e7
Source dataset
uspto-grants-1976_08
Patent number
US03976661

Reaction notes

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