Dichloromethane → Trichlorothiophene-3-sulfonyl chloride

HRID 1973914Notes

Reaction equation

HRID 1973914 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[CH:5][C:6]=1[S:7]([Cl:10])(=[O:9])=[O:8].C(Cl)[Cl:13]>S(Cl)(Cl)(=O)=O.O.[S]Cl.[Cl-].[Cl-].[Cl-].[Al+3]>[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[C:5]([Cl:13])[C:6]=1[S:7]([Cl:10])(=[O:8])=[O:9]

Participants

7

Reactant 2

HCID 6344DichloromethaneHCID 27360942,5-Dichlorothiophene-3-sulfonyl chloride

Product 1

HCID 16639974Trichlorothiophene-3-sulfonyl chloride

Reagents, catalysts & solvents 4

HCID 6451240Aluminum(III) ChlorideCatalystHCID 15930840CID 15930840CatalystHCID 962WaterSolventHCID 24648Sulfuryl chlorideSolvent2×

Procedure

A mixture of 63 g (0.25 mol) 2,5-dichlorothien-3-yl-sulfonyl chloride, 0.5 g sulfur monochloride and 25 g sulfuryl chloride was heated under reflux. To the refluxing reaction was then added dropwise 0.5 g aluminum trichloride in 25 g sulfuryl chloride. The reaction mixture was then heated under reflux for 3 hours, cooled diluted with 400 ml cold water and cooled, with methylene chloride. The methylene chloride extracts were washed with water, saturated aqueous sodium bicarbonate, dried over magnesium sulfate and stripped to give 62 g of 2,4,5-trichlorothien-3-ylsulfonyl chloride, which crystallized from hexane as a solid, m.p. 55° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customTo the refluxing reaction
  4. temperatureThe reaction mixture was then heated
  5. temperatureunder reflux for 3 hours
  6. temperaturecooled
  7. washThe methylene chloride extracts were washed with water, saturated aqueous sodium bicarbonate
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-66918658db194bf898b0c2b682c41b23
Source dataset
uspto-grants-1976_12
Patent number
US03998961

Reaction notes

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