Benzoyl chloride → N'-benzoyl-4-bromobenzohydrazide

HRID 2075609Notes

Reaction equation

HRID 2075609 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 81.1%

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-necked flask, 7 mL of N-methyl-2-pyrrolidone (abbr.: NMP) was added therein, and then 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 dropped through a 50-mL dropping funnel, and the mixture was stirred at 80° C. for three 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 as a target matter was obtained (yield: 80%).

Workup

  1. customabove was put in a 300-mL three-necked flask
  2. additionwas dropped through a 50-mL
  3. stirringthe mixture was stirred at 80° C. for three hours
  4. washThe obtained solid was washed with water
  5. filtrationa sodium carbonate aqueous solution in this order and collected by suction filtration
  6. customThen, the solid was recrystallized with acetone

Sources & evidence

ORD record
ord-1925b33ec7fc498eaed15f3e20987bff
Source dataset
uspto-grants-2011_04
Patent number
US07919773B2

Reaction notes

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