Azobisisobutyronitrile → HCID 19385626, compound

HRID 2399475Notes

Reaction equation

HRID 2399475 reaction equation
[C:1]([C:9]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:10]=1[O:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:28]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([C:9]1[CH:26]=[C:25]([CH2:27][Br:28])[CH:24]=[CH:23][C:10]=1[O:11][CH:12]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385721HCID 19385721, compound

Product 1

HCID 19385626HCID 19385626, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.314 g (0.87 mmol) of the product of Step A dissolved in 10 mL of CCl4 was added 0.155 g (0.87 mmol) of N-bromosuccinimide and 15 mg (catalytic amount) of AIBN. The mixture was stirred at reflux for 7 hours, then cooled filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 15% ethyl acetate/hexane to afford 0.136 g (36%) of the title compound.

Workup

  1. temperatureat reflux for 7 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d24d31619df349fbbdf37f71bb1210cd
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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