Azobisisobutyronitrile → Dimethyl 4-[2-(acetylthio)ethyl]-1,3-benzenedicarboxylate

HRID 1281219Notes

Reaction equation

HRID 1281219 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[C:13]([O:15][CH3:16])=[O:14])=[CH2:2].CC(N=NC(C#N)(C)C)(C#N)C.[C:29]([OH:32])(=[S:31])[CH3:30]>C1C=CC=CC=1.C([O-])(O)=O.[Na+]>[C:29]([S:31][CH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[C:13]([O:15][CH3:16])=[O:14])(=[O:32])[CH3:30]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 12017547Dimethyl 4-ethenyl-1,3-benzenedicarboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 12017548Dimethyl 4-[2-(acetylthio)ethyl]-1,3-benzenedicarboxylateYield 27%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a degassed solution of dimethyl 4-ethenyl-1,3-benzenedicarboxylate (415 mg, 1.88 mmol) in benzene (6 mL) were added AIBN (33 mg, 0.21 mmol) and thioacetic acid (0.27 mL, 3.78 mmol), and the mixture was refluxed for 5 hours. The reaction mixture was diluted with aqueous NaHCO3 solution (15 mL) and extracted with EtOAc (15 mL). The organic layer was dried over MgSO4 and concentrated. The residual material was purified by silica gel chromatography (hexanes/EtOAc=10:1) to give 0.150 g of colorless oil (27% yield).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionextracted with EtOAc (15 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residual material was purified by silica gel chromatography (hexanes/EtOAc=10:1)

Sources & evidence

ORD record
ord-a3d4ab7994e24cc7bbf9158147f81c68
Source dataset
uspto-grants-2002_09
Patent number
US06452044B2

Reaction notes

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