Sodium Thiosulfate → HCID 14390549, compound

HRID 2231282Notes

Reaction equation

HRID 2231282 reaction equation
[Cl:1][C:2]([Cl:18])=[CH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.ClC1C=CC=C(C(OO)=[O:27])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:18][C:2]([Cl:1])=[CH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])(=[O:27])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 14390548HCID 14390548, compound

Product 1

HCID 14390549HCID 14390549, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2,2-dichloroethenyl)-5-(4-methylsulfinylphenyl)thiophene (0.8 g, 0.0025 mole) and m-chloroperbenzoic acid (2.0 g, 0.005 mole) in methylene chloride (50 mL) was stirred at room temperature for two days. The mixture was poured into a 0.5N aqueous sodium thiosulfate solution. The resultant mixture was extracted with diethyl ether. The extract was washed first with an aqueous 10% sodium hydroxide solution, followed by an aqueous 10% hydrochloric acid solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, leaving a solid residue. This residue was purified by column chromatography on alumina, eluting with n-hexane:ethyl acetate (50:50), yielding 0.4 g of 2-(2,2-dichloroethenyl)-5-(4-methylsulfonylphenyl)thiophene as a solid (mp 143°-145° C.).

Workup

  1. extractionThe resultant mixture was extracted with diethyl ether
  2. washThe extract was washed first with an aqueous 10% sodium hydroxide solution
  3. extractionThe washed extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customleaving a solid residue
  8. customThis residue was purified by column chromatography on alumina
  9. washeluting with n-hexane:ethyl acetate (50:50)

Sources & evidence

ORD record
ord-e85b966490f9443ba5a39bcd8b8a6226
Source dataset
uspto-grants-1988_11
Patent number
US04782079

Reaction notes

Loading…