2,6-Dimethylaniline → (2,6-Dimethylanilino)acetonitrile

HRID 2285942Notes

Reaction equation

HRID 2285942 reaction equation
C1(S([O-])(=O)=O)C=CC=CC=1.[C:11](#[N:13])[CH3:12].[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17]>C(OCC)(=O)C>[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH:17][CH2:12][C:11]#[N:13]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 86738343HCID 86738343, compound

Product 1

HCID 20478053(2,6-Dimethylanilino)acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 158.5 g (0.804 mol) of benzenesulphonate-acetonitrile in 200 ml of ethyl acetate is run dropwise into a solution of 193.6 g (1.608 mols) of 2,6-dimethyl-aniline in 400 ml of ethyl acetate. The mixture is heated under reflux for 3 hours, cooled and the excess aniline benzenesulphonate is filtered off. The filtrate is evaporated to dryness. The residue is taken up in ether. Insoluble material is again filtered off and discarded. The ether is evaporated to dryness. The residue is taken up in a mixture of petroleum ether/benzene (3:4 v/v). The crystals which form are filtered off.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. filtrationthe excess aniline benzenesulphonate is filtered off
  5. customThe filtrate is evaporated to dryness
  6. filtrationInsoluble material is again filtered off
  7. customThe ether is evaporated to dryness
  8. additionThe residue is taken up in a mixture of petroleum ether/benzene (3:4 v/v)
  9. filtrationThe crystals which form are filtered off

Sources & evidence

ORD record
ord-80aecad225ff4701acbe0d42ff2af916
Source dataset
uspto-grants-1982_04
Patent number
US04325964

Reaction notes

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