Azobisisobutyronitrile → HCID 18536041, compound

HRID 412153Notes

Reaction equation

HRID 412153 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH3:13].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH2:13][Br:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18536178HCID 18536178, compound

Product 1

HCID 18536041HCID 18536041, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of the product from Step A (10.38 g, 39.2 mmol) and N-bromosuccinimide (8.61 g, 48.4 mmol) in 80 mL of carbontetrachloride was added 2,2′-azobisisobutyronitrile (0.89 g, 5.4 mmol), and the reaction was heated at reflux overnight under argon. The solution was cooled to room temperature, concentrated in vacuo, slurried with 30% EtOAc/hexane solution, and filtered. The filtrate was washed with saturated aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide a 2:1 mixture of the titled product and a tribromide as a yellow oil.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight under argon
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. washThe filtrate was washed with saturated aq. NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide

Sources & evidence

ORD record
ord-fafe44d265b6408d9ad0522c6804d18e
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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