Azobisisobutyronitrile → HCID 66812920, compound

HRID 1097977Notes

Reaction equation

HRID 1097977 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:14][CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 10058030HCID 10058030, compound

Product 1

HCID 66812920HCID 66812920, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of EXAMPLE 6B (2.37 g) in chloroform (30 mL) was added N-bromosuccinimide (2.41 g) and AIBN (4 mg), and the mixture was heated at reflux for 18 hours. After cooling, the solvent was removed, and the concentrate was partitioned between ethyl acetate and water. The extract was washed with brine and concentrated, and the concentrate was purified by flash chromatography on silica gel with 20% ethyl acetate in hexanes.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe solvent was removed
  5. customthe concentrate was partitioned between ethyl acetate and water
  6. washThe extract was washed with brine
  7. concentrationconcentrated
  8. customthe concentrate was purified by flash chromatography on silica gel with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8fe6d4d1f682457f9724a30085ca1786
Source dataset
uspto-grants-2012_03
Patent number
US08143284B2

Reaction notes

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