Hydrochloric Acid → HCID 80277746, compound

HRID 546662Notes

Reaction equation

HRID 546662 reaction equation
CS(CSC)=O.[OH-:7].[K+].[Cl:9][C:10]1[S:11][C:12]([CH:15]=[C:16](S(C)=O)SC)=[CH:13][CH:14]=1.Cl.[CH2:23]([OH:25])[CH3:24]>CO>[Cl:9][C:10]1[S:11][C:12]([CH2:15][C:16]([O:25][CH2:23][CH3:24])=[O:7])=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 86628502HCID 86628502, compound2×

Product 1

HCID 80277746HCID 80277746, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl methylsulfinylmethyl sulfide (5.53 g) and potassium hydroxide (2 g) were added to a solution of 5-chloro-2-thiophenecarboxyaldehyde (6.21 g) in methanol (70 mL), and the reaction solution was stirred with heating under reflux for 21 hours. After leaving to cool to room temperature, the solvent was evaporated under reduced pressure. Methylene chloride was added to the residue, the insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 5.61 g of a (E)/(Z) mixture of 2-chloro-5-(2-methanesulfinyl-2-methylsulfanylvinyl)thiophene. A saturated solution of hydrogen chloride in ethanol (10 mL) was added to a solution of the resulting (E)/(Z) mixture of 2-chloro-5-(2-methanesulfinyl-2-methylsulfanylvinyl)thiophene (5.61 g) in ethanol (80 mL), and the reaction solution was stirred with heating under reflux for 23 hours. After leaving to cool to room temperature, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 3.31 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 21 hours
  3. customAfter leaving
  4. customthe solvent was evaporated under reduced pressure
  5. additionMethylene chloride was added to the residue
  6. customthe insoluble matter was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThen, the residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)
  9. customto obtain 5.61 g of a (
  10. stirringthe reaction solution was stirred
  11. temperaturewith heating
  12. temperatureunder reflux for 23 hours
  13. customAfter leaving
  14. temperatureto cool to room temperature
  15. customthe solvent was evaporated under reduced pressure
  16. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-78fb94b8bdf64bd28b3b39ba8b42c8e5
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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