Ethanol → Benzoylhydrazine

HRID 1399470Notes

Reaction equation

HRID 1399470 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O.[NH2:16][NH2:17].O>C(OCC)(=O)C>[C:1]([NH:16][NH2:17])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 7165Ethyl benzoateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 11955BenzoylhydrazineYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
78 °C

Procedure

Into a 200 mL three-neck flask was put 25 g (0.17 mol) of ethyl benzoate, 60 mL of ethanol was added thereto, and the mixture was stirred. After that, 20 mL of hydrazine monohydrate was added to the mixture, and this mixture was stirred while being heated at 78° C. for 8 hours. After the reaction, the reaction solution was added to about 500 mL of water, and ethyl acetate was added to this aqueous solution. An organic layer was separated from an aqueous layer, and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution in that order. Magnesium sulfate was added to the organic layer, so that the organic layer was dried. This mixture was suction filtered, so that the magnesium sulfate was removed, whereby a filtrate was obtained. The obtained filtrate was concentrated to give a solid. The solid was recrystallized with a mixed solvent of ethanol and hexane, whereby 15 g of a white solid of benzohydrazide, which was the object of the synthesis, was obtained in a yield of 66% (synthesis scheme (b-1)).

Workup

  1. customInto a 200 mL three-neck flask was put
  2. stirringthis mixture was stirred
  3. customAfter the reaction
  4. additionwas added to this aqueous solution
  5. customAn organic layer was separated from an aqueous layer
  6. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  7. additionMagnesium sulfate was added to the organic layer, so that the organic layer
  8. customwas dried
  9. filtrationfiltered, so that the magnesium sulfate
  10. customwas removed
  11. customwhereby a filtrate was obtained
  12. concentrationThe obtained filtrate was concentrated
  13. customto give a solid
  14. customThe solid was recrystallized with a mixed solvent of ethanol and hexane, whereby 15 g of a white solid of benzohydrazide, which
  15. customthe object of the synthesis
  16. customwas obtained in a yield of 66% (synthesis scheme (b-1))

Sources & evidence

ORD record
ord-3ca065a9f49a48f99c2f07bb4dd0264d
Source dataset
uspto-grants-2014_12
Patent number
US08906518B2

Reaction notes

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