Ethanol → N-(2-methylaminobenzoyl)-N'-ethoxycarbonylhydrazine

HRID 251922

Reaction equation

HRID 251922 reaction equation
C[N:2]1[C:8](=O)[O:7][C:5](=O)[C:4]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:3]12.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[NH:15][NH2:16].C(O)C>C(OCC)(=O)C>[CH3:8][NH:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([NH:16][NH:15][C:14]([O:18][CH2:19][CH3:20])=[O:17])=[O:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 25160N-Methylisatoic anhydride

Product 1

HCID 13167844N-(2-methylaminobenzoyl)-N'-ethoxycarbonylhydrazineYield 50.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8.86 g of N-methylisatoic anhydride, 5.73 g of ethyl carbazate and 25 ml of ethanol was heated to reflux for 2 hours. After the reaction mixture was allowed to around room temperature, ethyl acetate was added thereto and the mixture was washed with water two times. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was washed with methyl tert-butyl ether to obtain 5.99 g of N-(2-methylaminobenzoyl)-N′-ethoxycarbonylhydrazine of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customwas allowed to around room temperature
  4. washthe mixture was washed with water two times
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting residue was washed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-4dee796b6fc0461ab963238e1978c11e
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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