Dichloromethane → HCID 23344803, compound

HRID 436359Notes

Reaction equation

HRID 436359 reaction equation
[C:1]([NH:5][NH2:6])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl[CH2:18][C:19](=O)[CH3:20]>CCCCC>[C:1]([N:5]=[N:6][C:19]([CH3:20])=[CH2:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6571ChloroacetoneHCID 24436Sodium SulfateHCID 81890tert-Butylhydrazine

Product 1

HCID 23344803HCID 23344803, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a solution of 6.75 g. (.007 m.) tert.-butylhydrazine in 50 ml. of methylene chloride containing 2 g. of anhydrous sodium sulfate, was added 3.0 g. (.0326 m.) chloroacetone. The addition was carried out dropwise holding the reaction temperature below 10° C. with an ice bath. The reaction was stirred and additional 45 minutes and filtered. The filtrate was washed with cold water (10° C.), dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated off using a rotating evaporator and a 20° C. water bath. A yellow oil containing some solids suspended in it was obtained. The crude material was slurried in cold pentane and filtered. The pentane was then evaporated off from the filtrate on the rotating evaporator. The yield was 1.9 g. (47%) of a yellow oil. The infra-red spectrum was consistent with the structure of the proposed compound. 2-tert.-butylazopropene is a thermally unstable compound and evolves nitrogen at room temperature and is therefore a very low temperature blowing agent.

Workup

  1. additionThe addition
  2. customthe reaction temperature below 10° C.
  3. filtrationfiltered
  4. washThe filtrate was washed with cold water (10° C.)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe methylene chloride evaporated off
  8. customa rotating evaporator
  9. customa 20° C. water bath
  10. additionA yellow oil containing some solids
  11. customwas obtained
  12. filtrationfiltered
  13. customThe pentane was then evaporated off from the filtrate on the rotating evaporator
  14. customat room temperature

Sources & evidence

ORD record
ord-b144b191d2304aceac1da8728ca01722
Source dataset
uspto-grants-1977_02
Patent number
US04008273

Reaction notes

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