P-Toluenesulfonylhydrazide → HCID 11469941, compound

HRID 1702222Notes

Reaction equation

HRID 1702222 reaction equation
[CH:1]([CH:3]1[CH2:5][C:4]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH2:2].S(NN)(C1C=CC(C)=CC=1)(=O)=O>COCCOCCOC>[CH2:1]([CH:3]1[CH2:5][C:4]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 111025Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

Product 1

HCID 11469941HCID 11469941, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Diethyl 2-vinylcyclopropane-1,1-dicarboxylate (5 g; 0.024 mol) was combined with 8.8 g (0.047 mol) tosyl hydrazine in 20 mls diglyme and the mixture heated with agitation to reflux for one hour. The reaction mixture was then allowed to cool and 2.73 g crude product obtained after washing with water and petroleum ether. The purified diethyl 2-ethylcyclopropane-1,1-dicarboxylate, obtained by distillation, contained 61.89% carbon and 8.33% hydrogen (calculated 61.66% C, 8.47% H) and the nuclear magnetic resonance spectra verified that the product was completely reduced.

Workup

  1. temperaturethe mixture heated with agitation
  2. temperatureto reflux for one hour
  3. temperatureto cool
  4. custom2.73 g crude product obtained
  5. washafter washing with water and petroleum ether

Sources & evidence

ORD record
ord-1fe8772a48814da597ef749f9b7397cc
Source dataset
uspto-grants-1983_04
Patent number
US04380656

Reaction notes

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