Benzoylhydrazine → HCID 25645622, compound

HRID 627824Notes

Reaction equation

HRID 627824 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.[CH3:18][C:19]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>O>[CH3:18][C:19]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 11955BenzoylhydrazineHCID 13387N-methyl-2-pyrrolidone2×HCID 28008992,3-Dimethylbenzoyl chloride

Product 1

HCID 25645622HCID 25645622, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 9.4 g (69.0 mmol) of benzoylhydrazine and 50 mL of N-methyl-2-pyrrolidinone (NMP) were put into a 300-mL three-neck flask and stiffed under nitrogen flow while being cooled with ice. To this mixed solution, a mixed solution of 13.0 g (77.1 mmol) of 2,3-dimethylbenzoyl chloride and 10 mL of NMP was slowly added dropwise, and the mixture was stiffed at room temperature for 24 hours. After reaction for the predetermined time, this reacted solution was slowly added to 500 mL of water, so that a white solid was precipitated. The precipitated solid was washed by repeating twice ultrasonic cleaning in which water and then 1M hydrochloric acid were used. Then, ultrasonic cleaning using hexane was performed, so that 16.9 g of a white solid of 1-(2,3-dimethylbenzoyl)-2-benzoylhydrazine was obtained in a yield of 91%. A synthesis scheme of Step 1 is shown in (d-1).

Workup

  1. temperaturewhile being cooled with ice
  2. customAfter reaction for the predetermined time
  3. customwas precipitated
  4. washThe precipitated solid was washed
  5. customwas obtained in a yield of 91%
  6. customA synthesis scheme of Step 1

Sources & evidence

ORD record
ord-71352a59f39f42798c1cf45060a8984e
Source dataset
uspto-grants-2016_04
Patent number
US09309458B2

Reaction notes

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