Azobisisobutyronitrile → HCID 67236432, compound

HRID 2402422Notes

Reaction equation

HRID 2402422 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-vinylbenzoic 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-f41ededf1b11404c9c08e284e795ae35
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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