Azobisisobutyronitrile → HCID 19385706, compound

HRID 2255574Notes

Reaction equation

HRID 2255574 reaction equation
[O:1]([CH:8]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[O:1]([CH:8]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][Br:20])=[CH:15][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385664HCID 19385664, compound

Product 1

HCID 19385706HCID 19385706, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a CCl4 solution (1 mL) of the product of Step B (126 mg, 0.495 mmol) was added N-bromosuccinimide (44 mg, 246 mmol) and a catalytic amount of AIBN. The solution was refluxed for 30 minutes and then concentrated in vacuo. The residue was purified on a silica gel flash chromatography column (150×30 mm) eluted with 5% ethyl acetate/hexane to afford 27 mg (33%) of the title compound.

Workup

  1. temperatureThe solution was refluxed for 30 minutes
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified on a silica gel flash chromatography column (150×30 mm)
  4. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-bec84bc97b0b44e1b9881d15f3cb086b
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

Loading…