P-Anisidine → [1-(4-Methoxyanilino)ethylidene]propanedinitrile

HRID 1576492Notes

Reaction equation

HRID 1576492 reaction equation
C(OCC)(OCC)O[CH2:3][CH3:4].[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[C:20](#[N:24])[CH2:21][C:22]#[N:23]>C(O)C>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:3](=[C:21]([C:20]#[N:24])[C:22]#[N:23])[CH3:4])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8010MalononitrileHCID 31214Ethyl orthoformate

Product 1

HCID 21510819[1-(4-Methoxyanilino)ethylidene]propanedinitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of triethyl orthoformate (29.6 g., 0.20 mole), 4-methoxyaniline (24.6 g., 0.20 mole) and malononitrile (13.2 g., 0.20 mole) in 250 ml. of ethanol are heated under reflux for 3 hours. The desired crystalline product separates on cooling. It is isolated by filtration and washed with ethanol. Recrystallization from equal parts of ethanol and acetone gives 28.5 g. of product having a melting point of 254°-255°C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureon cooling
  3. customIt is isolated by filtration
  4. washwashed with ethanol
  5. customRecrystallization from equal parts of ethanol and acetone
  6. customgives 28.5 g

Sources & evidence

ORD record
ord-c337ee915adf44afae213f540a9bbec9
Source dataset
uspto-grants-1976_09
Patent number
US03981717

Reaction notes

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