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

HRID 23592Notes

Reaction equation

HRID 23592 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-2fd6baa986b74fccad2714dfe20d51dd
Source dataset
uspto-grants-2005_02
Patent number
US06852750B2

Reaction notes

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