Benzene → HCID 14230910, compound

HRID 620810Notes

Reaction equation

HRID 620810 reaction equation
S(Cl)(Cl)=O.O[C:6]1[S:7][C:8](=[C:11]([S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:12]([O-:14])=[O:13])[S:9][CH:10]=1.[CH:21]1[CH:26]=CC=C[CH:22]=1.C(N(CC)CC)C>O>[S:9]1[CH:10]=[CH:6][S:7][C:8]1=[C:11]([S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:12]([O:14][CH:21]([CH3:26])[CH3:22])=[O:13]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 178461032HCID 178461032, compound

Product 1

HCID 14230910HCID 14230910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After dropwise addition of 13.5 g of thionyl chloride to a mixture of 32.7 g of 4-hydroxy-1,3-dithiol-2-ylidene-isopropylsulfonylacetate and 100 ml of benzene, the reaction mixture was refluxed for 30 minutes. Subsequent to its cooling, 13.0 g of triethylamine was added to the reaction solution, followed by further reflux for 3 hours. The resultant reaction mixture was cooled. Water was added to the reaction mixture and the resulting organic layer was separated. Upon removal of the solvent by distillation under reduced pressure, 28.3 g of the title compound was obtained as pale brown crystals. Upon recrystallization from a mixed solvent of benzene and n-hexane, they turned to white crystals. Melting point: 124.5°-125° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. temperatureSubsequent to its cooling
  3. temperatureby further reflux for 3 hours
  4. customThe resultant reaction mixture
  5. temperaturewas cooled
  6. customthe resulting organic layer was separated
  7. customUpon removal of the solvent
  8. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-5d70ac9acc3341da880849f47937af43
Source dataset
uspto-grants-1989_04
Patent number
US04822814

Reaction notes

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