Azobisisobutyronitrile → HCID 19385678, compound

HRID 2255585Notes

Reaction equation

HRID 2255585 reaction equation
[C:1]([C:4]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2].[Br:23]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([C:4]1[CH:21]=[C:20]([CH2:22][Br:23])[CH:19]=[CH:18][C:5]=1[O:6][CH:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385744HCID 19385744, compound

Product 1

HCID 19385678HCID 19385678, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1.25 g (4.19 mmol) of the product of Step A dissolved in 15 mL of CCl4 was added 0.821 g (4.61 mmol) of N-bromosuccinimide and 20 mg (catalytic amount) of AIBN. The mixture was stirred at reflux for 3.5 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 0.431 g (27%) yield of the title compound.

Workup

  1. temperatureat reflux for 3.5 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-c51d6a61b3dd42b781c652a6b833aab5
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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