2-Chlorocyclohexanone → HCID 23344749, compound

HRID 1414166Notes

Reaction equation

HRID 1414166 reaction equation
[C:1]([NH:5][NH2:6])([CH3:4])([CH3:3])[CH3:2].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:14]1[CH2:20][CH:19](Cl)[C:17](=O)[CH2:16][CH2:15]1>C(Cl)Cl>[C:1]([N:5]=[N:6][C:14]1[CH2:20][CH2:19][CH2:17][CH2:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 132032-ChlorocyclohexanoneHCID 24436Sodium SulfateHCID 81890tert-Butylhydrazine

Product 1

HCID 23344749HCID 23344749, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11 g. (.125 m.) tert.-butylhydrazine in 80 ml. of methylene chloride containing 2 g. anhydrous sodium sulfate, was added 6.8 g. (0.052 m.) alpha-chlorocyclohexanone. The addition was carried out dropwise and the reaction temperature was maintained at 20° C. ±5° by an ice bath. The solution immediately turned yellow, but the reaction was stirred for an additional 1 hour after the addition was complete before filtering it. The filtered methylene chloride solution was washed with 100 ml. water, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated off. A viscous, gelatinous liquid remained. The material was cooled in the freezer and then filtered. A white solid, 0.1 g., remained on the filter. The filtrate weighed 8.4 g. (97% yield) and its infra-red spectrum was consistent with the proposed structure. It showed the absence of N-H and carbonyl bands and the presence of a carbon-carbon double bond (1650 cm-1) and a conjugated azo bond (1510 cm-1). The product evolves nitrogen at 60 ° C. 1(-tert.-butylazo)eyeclohexane gelled the unsaturated polyester-styrene resin of Example III at room temperature.

Workup

  1. additionThe addition
  2. temperaturethe reaction temperature was maintained at 20° C. ±5° by an ice bath
  3. additionafter the addition
  4. filtrationbefore filtering it
  5. washThe filtered methylene chloride solution was washed with 100 ml
  6. dry with materialwater, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe methylene chloride evaporated off
  9. temperatureThe material was cooled in the freezer
  10. filtrationfiltered
  11. customat 60 ° C
  12. customat room temperature

Sources & evidence

ORD record
ord-65ecb4e0be3849789d7e9145ba96a898
Source dataset
uspto-grants-1977_01
Patent number
US04001207

Reaction notes

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