HCID 12695535, compound → HCID 22404777, compound

HRID 440676Notes

Reaction equation

HRID 440676 reaction equation
Br[CH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[O:4][C:3]1([CH3:15])[CH3:14].[S:16]([O-])([O-])(=O)=S.C([N+](CC)(CC)CC)C.C([N+](CC)(CC)CC)C>C(O)C.C(OCC)C.C(Cl)Cl>[CH3:14][C:3]1([CH3:15])[C:2](=[S:16])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[O:4]1

Participants

6

Reactant 2

HCID 12695535HCID 12695535, compoundHCID 22404724HCID 22404724, compound

Product 1

HCID 22404777HCID 22404777, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In a flask are placed 5.44 g (0.020 mole) of 3-bromo-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran (prepared by the method of Example 2, Step A) and 7.45 g (0.020 mole) of tetraethylammonium thiosulfate (prepared by the method of B. Hahn et al., Liebigs Ann. Chem. 1981, 10-19) in 100 mL of absolute ethanol. This mixture is heated at reflux for 24 hours after which the solvent is removed under reduced pressure, leaving a residue. This residue is taken up in 60 mL of diethyl ether which is then filtered to remove inorganic salts. Slowly, 20 mL of a 2N aqueous sodium hydroxide solution is added to the rapidly stirred filtrate. This mixture is stirred for 30 minutes at room temperature after which the aqueous phase is separated from the organic phase. The latter is washed with water, dried over anhydrous sodium sulfate, and filtered. The solvent is evaporated under reduced pressure, leaving a residue which is dissolved in methylene chloride. This solution is passed through a column of silica gel, eluting with methylene chloride. Product-containing fractions are combined, and the solvent is evaporated under reduced pressure, yielding 2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-thione.

Workup

  1. customIn a flask are placed
  2. customprepared by the method of B
  3. temperatureThis mixture is heated
  4. temperatureat reflux for 24 hours after which the solvent
  5. customis removed under reduced pressure
  6. customleaving a residue
  7. filtrationis then filtered
  8. customto remove inorganic salts
  9. additionSlowly, 20 mL of a 2N aqueous sodium hydroxide solution is added to the rapidly stirred filtrate
  10. customis separated from the organic phase
  11. washThe latter is washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customThe solvent is evaporated under reduced pressure
  15. customleaving a residue which
  16. washeluting with methylene chloride
  17. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-f505d7a3e9c44df3ae3601d316f9a288
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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