Azobisisobutyronitrile → HCID 67236432, compound

HRID 1264358Notes

Reaction equation

HRID 1264358 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[C:12]1([SH:18])C=CC=C[CH:13]=1.[CH3:19][C:20](N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[S:18]1[CH:12]=[CH:13][CH:2]=[C:1]1[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH2:19][CH3:20])[CH:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7969ThiophenolHCID 140984-Vinylbenzoic acid

Product 1

HCID 67236432HCID 67236432, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

According to the published procedure (Gareau et al., Tet. Lett., 1994, 1837), under nitrogen atmosphere in a 50 mL round bottomed flask containing 4-vinyl-benzoic acid (1.0 g, 6.75 mmoles) in 10 mL of benzene (0.7 M) was added benzenethiol (797 μL, 7.76 mmoles) followed by VAZO™ (Aldrich Chemical Company, 495 mg, 2.02 mmoles). The mixture was stirred for 12 hours at reflux. The resulting solution was cooled at room temperature and the solvent was evaporated under vacuo. The solid was purified by trituration using hexane and dichloromethane to afford 1.94 g (85%) of white solid.

Workup

  1. customAccording to the published procedure (Gareau et al., Tet. Lett., 1994, 1837), under nitrogen atmosphere in a 50 mL round bottomed flask
  2. temperatureat reflux
  3. customthe solvent was evaporated under vacuo
  4. customThe solid was purified by trituration

Sources & evidence

ORD record
ord-d9d42b92b96c4beab642eb613b8cf00c
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Reaction notes

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