1,1-Dimethylhydrazine → HCID 13745532, compound

HRID 568941Notes

Reaction equation

HRID 568941 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13].CN(C)N>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:11]1[C:10](=[O:15])[CH:11]=[C:12]([CH3:13])[O:14][C:12]=1[CH3:13])=[O:15]

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 296091N-(Dimethylphenyl)-3-oxobutyramide

Product 1

HCID 13745532HCID 13745532, compoundYield 126.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 10.3 g (50 m mol) of N-(2,3-dimethylphenyl)-3-oxo-butanamide, 4.50 g (75 m mol) of N,N-dimethylhydrazine and 60 ml of toluene was stirred for 8 hours at 60° C. Then, unreacted N,N-dimethylhydrazine and the resulting water together with about 10 ml of toluene were distilled off outside the reaction system. 10.5 g (125 m mol) of diketene was added dropwise to the remaining solution over a period of 5 minutes, while refluxing. The mixture was further refluxed for 2 hours and cooled to room temperature. The resulting crystals were filtered, washed and dried to obtain 8.63 g (yield 64%) of the title compound.

Workup

  1. distillationThen, unreacted N,N-dimethylhydrazine and the resulting water together with about 10 ml of toluene were distilled off outside the reaction system
  2. addition10.5 g (125 m mol) of diketene was added dropwise to the remaining solution over a period of 5 minutes
  3. temperaturewhile refluxing
  4. temperatureThe mixture was further refluxed for 2 hours
  5. temperaturecooled to room temperature
  6. filtrationThe resulting crystals were filtered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-442ead4f9a1a460980d8ae621e4c58e0
Source dataset
uspto-grants-1988_03
Patent number
US04730061

Reaction notes

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