Sodium Hydroxide → 1,1'-Azobis(cyclohexanecarbonitrile)

HRID 464111Notes

Reaction equation

HRID 464111 reaction equation
[OH-].[Na+].[NH2:3][C:4]1([C:10]#[N:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>CCCCCCCCCCCCCCCC[N+](C)(C)C.[Cl-]>[N:3]([C:4]1([C:10]#[N:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[N:3][C:4]1([C:10]#[N:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 796351-Aminocyclohexanecarbonitrile

Product 1

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)Yield 162.2%

Reagents, catalysts & solvents 1

HCID 8154Hexadecyltrimethylammonium chlorideCatalyst

Conditions

Temperature
20 °C

Procedure

The pH is adjusted to 7 at 20° C. and 3 ml of `Arquad 16-29` is added followed by a further 2.2 equivalents of caustic soda and 23 g of 1-amino-1-cyanocyclohexane over 20 minutes with cooling to maintain a temperature of 20° C. The reaction is stirred for a further five minutes and filtered, washed and dried to yield 36.7 g of the title compound, as a white solid (89%).

Workup

  1. customis adjusted to 7 at 20° C.
  2. temperaturewith cooling
  3. filtrationfiltered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-4c8305cc724447428b153bf615f9fe5f
Source dataset
uspto-grants-1985_10
Patent number
US04546174

Reaction notes

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