Azobisisobutyronitrile → HCID 19385631, compound

HRID 2255589Notes

Reaction equation

HRID 2255589 reaction equation
[C:1]([C:5]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:6]=1[O:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[Br:24]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:22]=[C:21]([CH2:23][Br:24])[CH:20]=[CH:19][C:6]=1[O:7][CH:8]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:9]([O:11][CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385684HCID 19385684, compound

Product 1

HCID 19385631HCID 19385631, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.494 g (1.58 mmol) of the product of Step A dissolved in 10 mL of CCl4 was added 0.310 g (1.74 mmol) of N-bromosuccinimide and 15 mg (catalytic amount) of AIBN and the mixture was heated at reflux for 3.5 hours. The reaction was cooled, filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 3% ethyl acetate/hexane to afford 0.134 g (22%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3.5 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with 3% ethyl acetate/hexane

Sources & evidence

ORD record
ord-41752e2f38534c2d85e752c8bc2d8a4c
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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