Azobisisobutyronitrile → HCID 15457065, compound

HRID 1385940Notes

Reaction equation

HRID 1385940 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)=[C:4]([F:21])[CH:3]=1.C1C(=O)N([Br:29])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([CH2:8][Br:29])=[CH:6][C:5]([C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=2)=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 15457188HCID 15457188, compound

Product 1

HCID 15457065HCID 15457065, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.63 g (8.23 mmol) of 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 1.46 g (8.23 mmol) of NBS were dissolved in 100 ml of carbon tetrachloride. Then, 0.27 g (1.67 mmol) of 2,2′-azobisisobutyronitrile was slowly added thereto with stirring under heating and refluxing. Then, the mixture was further reacted for 5 hours. After cooling, the insoluble substances were filtered off, and the organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.67 g (yield: 81%) of the desired product. Melting point: 117-118° C.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. customThen, the mixture was further reacted for 5 hours
  4. temperatureAfter cooling
  5. filtrationthe insoluble substances were filtered off
  6. washthe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5f8b6b99718b4f0aae5007b9cabb5bfb
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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