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Benzoyl chloride → Benzoic acid, 2-benzoylhydrazide

HRID 2045747
Notes
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Reaction equation

HRID 2045747 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][NH2:10])=[O:8])=[CH:3][CH:2]=1.CN1CCCC1=O.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:7]([NH:9][NH:10][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:8])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11955BenzoylhydrazineHCID 13387N-methyl-2-pyrrolidone2×

Product 1

HCID 13085Benzoic acid, 2-benzoylhydrazide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 10 g (73 mmol) of benzohydrazine was put into a 300 mL three-neck flask, 25 mL of N-methyl-2-pyrrolidone was added thereto, and the mixture was stirred, a mixed solution of 10 mL of N-methyl-2-pyrrolidone and 10 mL (88 mmol) of benzoyl chloride was dripped into the mixture through a 50 mL dropping funnel. The mixture was stirred at 80° C. for 3 hours, and the contents of the flask were reacted together. After the reaction, the reaction solution was added to approximately 500 mL of water and the mixture was stirred, so that a solid was precipitated out. The precipitated solid was collected by suction filtration. The collected solid was washed with water, methanol was added to the obtained solid, and the mixture was washed, so that 10 g of a powdery white solid, which was the object of the synthesis, was obtained at a yield of 57%.

Workup

  1. stirringThe mixture was stirred at 80° C. for 3 hours
  2. customthe contents of the flask were reacted together
  3. customAfter the reaction
  4. stirringthe mixture was stirred, so that a solid
  5. customwas precipitated out
  6. filtrationThe precipitated solid was collected by suction filtration
  7. washThe collected solid was washed with water, methanol
  8. additionwas added to the obtained solid
  9. washthe mixture was washed, so that 10 g of a powdery white solid, which
  10. customthe object of the synthesis
  11. customwas obtained at a yield of 57%

Sources & evidence

ORD record
ord-7e96516775114fa89991c144018a7ba7
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592056B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes