Benzoyl chloride → Benzoic acid, 2-benzoylhydrazide

HRID 2176337Notes

Reaction equation

HRID 2176337 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

Participants

5

Reactant 3

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

Product 1

HCID 13085Benzoic acid, 2-benzoylhydrazideYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 6.6 g of benzoylhydrazine and 50 mL of N-methyl-2-pyrrolidone (NMP) were put in a 200 mL three-neck flask, and mixed. Then, a mixed solution of 5 mL of benzoyl chloride and 10 mL of NMP was dripped to the above mixed solution through a 50 mL dropping funnel, and stirred at room temperature for 1 hour to be reacted. The reacted mixed solution was added to 250 mL of water, and a white solid was precipitated. The precipitated solid was washed with 1M hydrochloric acid and subjected to suction filtration to give a white solid. The given solid was washed with methanol, so that N,N′-dibenzoylhydrazine was prepared (a white solid, yield: 65%). The synthetic scheme of Step 1 is shown by (a-6).

Workup

  1. additionmixed
  2. customto be reacted
  3. additionThe reacted mixed solution
  4. customa white solid was precipitated
  5. washThe precipitated solid was washed with 1M hydrochloric acid
  6. filtrationsubjected to suction filtration
  7. customto give a white solid
  8. washThe given solid was washed with methanol, so that N,N′-dibenzoylhydrazine
  9. customwas prepared (a white solid, yield: 65%)

Sources & evidence

ORD record
ord-f95658f3c45b4673b839ff5b24a84cbc
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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