Cyclohexanone → HCID 23344798, compound

HRID 1579163Notes

Reaction equation

HRID 1579163 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[C-:8]#[N:9].[Na+].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>O.CCCCCC>[C:2]([NH:6][NH:7][C:11]1([C:8]#[N:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 8929Sodium CyanideHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 23344798HCID 23344798, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8058HexaneSolvent2×

Procedure

To a rapidly stirred solution of 62.4 grams (0.50 moles) of t-butylhydrazine hydrochloride and 25.8 grams (0.525 moles) of sodium cyanide in 450 ml of water in a 11/2 liter jacketed resin reactor equipped with a thermometer, mechanical stirrer, condenser and dropping funnel was added 49 grams (0.5 moles) of cyclohexanone. The reaction mixture exothermed to about 35°C. The reaction was then warmed to 45°-50°C by circulating hot water through the jacket. The reaction was stirred 11/2 hours at 45°-50°C and then 100 ml of hexane was added to dissolve the solid hydrazo. The temperature had to be kept at 40°C or above to completely dissolve the hydrazo in the hexane. The aqueous layer was separated into 10% sodium hydroxide and set aside in the hood for detoxicafication by sodium hypochlorite solution. The hexane solution was washed with 400 ml of warm water and the wash separated at 40°C or above. A small sample of the hexane solution was dried, the hexane evaporated and an infrared spectrum run on the resultant solid. The infrared spectrum contained strong NH bands and a cyano band and did not contain any carbonyl or imino bands. Thus, the infrared spectrum was consistent with the structure of the desired product.

Workup

  1. customequipped with a thermometer, mechanical stirrer, condenser
  2. customexothermed to about 35°C
  3. temperatureThe reaction was then warmed to 45°-50°C
  4. dissolutionto dissolve the solid hydrazo
  5. customto be kept at 40°C or above
  6. customThe aqueous layer was separated into 10% sodium hydroxide
  7. washThe hexane solution was washed with 400 ml of warm water
  8. customthe wash separated at 40°C or above
  9. dry with materialA small sample of the hexane solution was dried
  10. customthe hexane evaporated

Sources & evidence

ORD record
ord-90bcc49a60cd4c2493395af0564c18be
Source dataset
uspto-grants-1976_01
Patent number
US03931143

Reaction notes

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