Benzoyl chloride → N'-benzoyl-4-bromobenzohydrazide

HRID 516480Notes

Reaction equation

HRID 516480 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1CCCC1=O>[C:12]([NH:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 222194-Bromobenzohydrazide2×

Product 1

HCID 3789270N'-benzoyl-4-bromobenzohydrazideYield 80%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Subsequently, 2.0 g (13.9 mmol) of the 4-bromobenzohydrazide obtained in (i) above was put in a 300-mL three-neck flask, 7 mL of N-methyl-2-pyrrolidone (abbreviation: NMP) was added thereto, and the mixture was stirred. Thereafter, a mixture of 2.5 mL of N-methyl-2-pyrrolidone and 2.5 mL (21.5 mmol) of benzoyl chloride was dripped through a 50-mL dropping funnel, and the mixture was stirred at 80° C. for 3 hours. The obtained solid was washed with water and a sodium carbonate aqueous solution in this order and collected by suction filtration. Then, the solid was recrystallized with acetone; thus, 3.6 g of a white solid of 1-benzoyl-2-(4-bromobenzoyl)hydrazine that was an object was obtained in the yield of 80%.

Workup

  1. customabove was put in a 300-mL three-neck flask
  2. stirringthe mixture was stirred at 80° C. for 3 hours
  3. washThe obtained solid was washed with water
  4. filtrationa sodium carbonate aqueous solution in this order and collected by suction filtration
  5. customThen, the solid was recrystallized with acetone
  6. customwas obtained in the yield of 80%

Sources & evidence

ORD record
ord-316e863fba134d848788ff7fb569cca5
Source dataset
uspto-grants-2015_08
Patent number
US09112170B2

Reaction notes

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