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Benzoyl chloride → Benzoic acid, 2-benzoylhydrazide

HRID 423235
Notes
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Reaction equation

HRID 423235 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCCC1=O.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:1]([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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 13085Benzoic acid, 2-benzoylhydrazideYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 300 mL three-neck flask was put 10 g (73 mmol) of benzohydrazide, and 25 mL of N-methyl-2-pyrrolidone was added thereto, and the mixture was stirred. After that, 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. This mixture was stirred at 80° C. for 3 hours, and the contents of the flask were reacted. After the reaction, the reaction solution was added to about 500 mL of water and the mixture was stirred, so that a solid was precipitated. The precipitated solid was collected by suction filtration. The collected solid was washed with water, and methanol was added to the obtained solid so that the solid was washed to give 10 g of a powdery white solid of 1,2-dibenzoylhydrazine, which was the object of the synthesis, at a yield of 57%.

Workup

  1. customInto a 300 mL three-neck flask was put
  2. stirringThis mixture was stirred at 80° C. for 3 hours
  3. customthe contents of the flask were reacted
  4. customAfter the reaction
  5. stirringthe mixture was stirred, so that a solid
  6. customwas precipitated
  7. filtrationThe precipitated solid was collected by suction filtration
  8. washThe collected solid was washed with water, and methanol
  9. additionwas added to the obtained solid so that the solid
  10. washwas washed

Sources & evidence

ORD record
ord-de54435188974b6ebe86d014c6b5cba9
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101771B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes