Azobisisobutyronitrile → HCID 59235189, compound

HRID 1919788Notes

Reaction equation

HRID 1919788 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[CH3:21][O:22][C:23](=[O:35])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=1>C(Cl)(Cl)(Cl)Cl>[C:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH:24]([Br:8])[C:23]([O:22][CH3:21])=[O:35])=[CH:26][CH:27]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 572417methyl (4-acetoxyphenyl)acetate

Product 1

HCID 59235189HCID 59235189, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

9.5 g of NBS and 0.7 g of AIBN are added to a solution of 10 g of methyl(4-acetoxyphenyl)acetate in 100 mL of carbon tetrachloride in a 500 mL flask equipped with a magnetic stirrer and a condenser. After 16 hours under reflux, the mixture is filtered, the solid is washed with dichloromethane then the filtrate is concentrated. The residue is purified over a silica column with pure dichloromethane to yield 13 mg of expected product (oil, Yd=95%).

Workup

  1. customequipped with a magnetic stirrer and a condenser
  2. temperatureAfter 16 hours under reflux
  3. filtrationthe mixture is filtered
  4. washthe solid is washed with dichloromethane
  5. concentrationthe filtrate is concentrated
  6. customThe residue is purified over a silica column with pure dichloromethane

Sources & evidence

ORD record
ord-4e71fb4c4b3a49edb90516428863d621
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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