Azobisisobutyronitrile → HCID 19365541, compound

HRID 1600064Notes

Reaction equation

HRID 1600064 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:33][C:13]3[N:14]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:15]=[C:16]([S:19]([CH:21]([CH3:23])[CH3:22])=[O:20])[C:17](=[O:18])[C:12]=3[C:11]=2[CH3:34])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:35]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:33][C:13]3[N:14]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:15]=[C:16]([S:19]([CH:21]([CH3:23])[CH3:22])=[O:20])[C:17](=[O:18])[C:12]=3[C:11]=2[CH2:34][Br:35])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19365602HCID 19365602, compound

Product 1

HCID 19365541HCID 19365541, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The compound (980 mg, 2 mmol) obtained in Example 17, N-bromosuccinimide (NBS) (0.36 g, 2.04 mmol) and α,α-azobisisobutyronitrile (AIBN) (60 mg, 0.37 mmol) were suspended in carbon tetrachloride (250 ml).The mixture was refluxed under heating for 3 hours. After cooling, the reaction mixture was partitioned between chloroform (300 ml) and an aqueous sodium bicarbonate solution. The aqueous layer was extracted with chloroform (100 ml), the extracts were combined, washed with an aqueous sodium chloride solution, dried with Na2SO4, and the solvent was distilled off. Thus obtained residue was recrystallized from dichloromethane-n-hexane to give yellow crystals (1.09 g, 96%).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between chloroform (300 ml)
  5. extractionThe aqueous layer was extracted with chloroform (100 ml)
  6. washwashed with an aqueous sodium chloride solution
  7. dry with materialdried with Na2SO4
  8. distillationthe solvent was distilled off
  9. customThus obtained residue was recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-e6d37a092d7b495cb89ad1a750aac45f
Source dataset
uspto-grants-1998_04
Patent number
US05744479

Reaction notes

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