Dichloromethane → Cyclohexanecarbonitrile, 1-[(1,1-dimethylethyl)azo]-

HRID 2071858Notes

Reaction equation

HRID 2071858 reaction equation
[C:1]([NH:5][NH:6][C:7]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.ClCl>O>[C:1]([N:5]=[N:6][C:7]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24526ChlorineHCID 23344798HCID 23344798, compound

Product 1

HCID 91298Cyclohexanecarbonitrile, 1-[(1,1-dimethylethyl)azo]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a rapidly stirred mixture of 39.0 g. (0.2 m. ) 1-tert.-butylhydrazo-1-cyanocyclohexane, 200 ml. methylene chloride and 100 ml. water was added 14.3 g. (0.2 m.) chlorine at such a rate that the reaction temperature did not exceed 5 ° C. The reaction was stirred an additional 15 mins. after the addition was complete. The methylene chloride layer was separated, washed twice with 50 ml. portions of saturated NaHCO3 solution, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated on a rotating evaporator to obtain 35.0 g. of liquid product that assayed 86.5% by an ultra violet spectrophotometric analysis. Distillation gavea product, b.p. 71° C./1.2 mm. of Hg that assayed 97.6% as 1-tert.-butylazo-1-cyanocyclohexane. The infrared spectrum was in accord with this structure.

Workup

  1. additionTo a rapidly stirred mixture of 39.0 g
  2. customdid not exceed 5 ° C
  3. additionafter the addition
  4. customThe methylene chloride layer was separated
  5. washwashed twice with 50 ml
  6. dry with materialportions of saturated NaHCO3 solution, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe methylene chloride evaporated on a rotating evaporator
  9. customto obtain 35.0 g
  10. distillationDistillation

Sources & evidence

ORD record
ord-533aebda8f1640b583cc4b1ef91e4fe6
Source dataset
uspto-grants-1977_09
Patent number
US04048423

Reaction notes

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