Azobisisobutyronitrile → HCID 19385691, compound

HRID 2399510Notes

Reaction equation

HRID 2399510 reaction equation
[CH3:1][C:2]1([C:8]2[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:9]=2[O:10][CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br:27]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:26][C:24]1[CH:23]=[CH:22][C:9]([O:10][CH:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:12]([O:14][CH3:15])=[O:13])=[C:8]([C:2]2([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)[CH:25]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385679HCID 19385679, compound

Product 1

HCID 19385691HCID 19385691, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.780 g (2.21 mmol) of the product of Step A dissolved in 12 mL of CCl4 was added 0.394 g (2.21 mmol) of N-bromosuccinimide and 20 mg (catalytic amount) of AIBN. The mixture was stirred and refluxed under a N2 atmosphere for 6 hours. The mixture was then cooled, filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 7% ethyl acetate/hexane to afford 0.203 g (21%) of the title compound.

Workup

  1. temperaturerefluxed under a N2 atmosphere for 6 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 7% ethyl acetate/hexane

Sources & evidence

ORD record
ord-71101827716f40cbbb1cc04dfb17f2c8
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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