2-Amino-2,4-dimethylpentanenitrile → 2,2'-Azobis(2,4-dimethylvaleronitrile)

HRID 1680123Notes

Reaction equation

HRID 1680123 reaction equation
Cl[O-].[Na+].[NH2:4][C:5]([CH3:12])([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]#[N:7]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[N:4]([C:5]([CH3:12])([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]#[N:7])=[N:4][C:5]([CH3:12])([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]#[N:7]

Participants

5

Reactant 2

HCID 922512-Amino-2,4-dimethylpentanenitrileHCID 23665760Sodium Hypochlorite

Product 1

HCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Next, 213 g of a 10% aqueous sodium hypochlorite solution was cooled to 5° C. and 0.5 g of benzyltriethylammonium chloride was added thereto. To the resulting aqueous solution was added 200 ml of an ethyl acetate solution containing 33 g of the resulting 90%-pure 2-amino-2,4-dimethylpentanonitrile over 30 minutes with stirring. This reaction mixture was stirred at 5° to 10° C. for 3 hours, and the organic and water phases were separated from each other. Ethyl acetate was removed from the organic phase under reduced pressure. The resulting white crystals were washed with water and dried to obtain 24.8 g of 2,2'-azobis(2,4-dimethylpentanonitrile). Yield was 85 mole %.

Workup

  1. stirringThis reaction mixture was stirred at 5° to 10° C. for 3 hours
  2. customthe organic and water phases were separated from each other
  3. customEthyl acetate was removed from the organic phase under reduced pressure
  4. washThe resulting white crystals were washed with water
  5. customdried

Sources & evidence

ORD record
ord-576ef44274384349824c609c27eacc47
Source dataset
uspto-grants-1981_06
Patent number
US04272435

Reaction notes

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