Thiophenol → HCID 402511, compound

HRID 276974Notes

Reaction equation

HRID 276974 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10](=[O:12])[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[C:25]1([SH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[C:25]1([S:31][CH2:2][C:3]2[CH:4]=[CH:5][C:6]3[O:11][C:10](=[O:12])[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]=3[CH:18]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 10659438Ethyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylate

Product 1

HCID 402511HCID 402511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1 g of ethyl 6-chloromethyl-2-oxo-2H-1-benzopyran-3-carboxylate (3.75 mmol), 0.57 g of potassium carbonate (4.13 mmol), 2.07 g of thiophenol (18.75 mmol) and 10 ml of absolute ethanol is reflux for 3 h. After removal of the solvent by distillation under reduced pressure, the residue is taken up in chloroform. The organic phase is washed with water and then dried over MgSO4. The solvent is removed by distillation under reduced pressure and the residue is washed with hexane to remove the excess thiophenol. The title product is recrystallized from ethyl acetate/petroleum ether.

Workup

  1. temperatureis reflux for 3 h
  2. customAfter removal of the solvent
  3. distillationby distillation under reduced pressure
  4. washThe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent is removed by distillation under reduced pressure
  7. washthe residue is washed with hexane
  8. customto remove the excess thiophenol
  9. customThe title product is recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-bc3cf4d6f6734b04aa103da6ccae100d
Source dataset
uspto-grants-2002_03
Patent number
US06355658B1

Reaction notes

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