Ethanol → ethyl 2-phenylhydrazinecarboxylate

HRID 973536Notes

Reaction equation

HRID 973536 reaction equation
C(O)C.[C:4]1([NH:10][NH2:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(N(CC)CC)C>[C:4]1([NH:10][NH:11][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7516PhenylhydrazineHCID 10928Ethyl chloroformate

Product 1

HCID 269262ethyl 2-phenylhydrazinecarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 200 ml of ethanol were poured 21.6 g (0.2 mol) of phenylhydrazine and 30 ml of triethylamine, and 21.6 g (0.2 mol) of ethyl chloroformate was slowly added dropwise thereto. After the addition, the mixture was refluxed for 30 minutes and then poured into ice-water. The mixture was extracted with ethyl acetate, and the extract was concentrated and purified by column chromatography to obtain 31 g of N-phenyl-N'-ethoxycarbonylhydrazine as an oily substance.

Workup

  1. additionwas slowly added dropwise
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 30 minutes
  4. extractionThe mixture was extracted with ethyl acetate
  5. concentrationthe extract was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-fcb18e7c7ef749129f477e7547fc9031
Source dataset
uspto-grants-1991_11
Patent number
US05064751

Reaction notes

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