2-Chlorothiophene → 5-Chlorothiophene-2-sulfonyl chloride

HRID 1973152Notes

Reaction equation

HRID 1973152 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C(=O)=O.CC(C)=O.[Cl:14][S:15](O)(=[O:17])=[O:16]>>[Cl:1][C:2]1[S:3][C:4]([S:15]([Cl:14])(=[O:17])=[O:16])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 72992-ChlorothiopheneHCID 24638Chlorosulfonic acidHCID 18522661Acetone cardice

Product 1

HCID 27339255-Chlorothiophene-2-sulfonyl chloride

Conditions

Temperature
50 °C

Procedure

An 80-g (0.68 mol) sample of 2-chlorothiophene was added dropwise to a cooled (dry ice/acetone bath, about -10° to -15° C.) and stirred solution of 160 g (1.38 mol) of chlorosulfonic acid. After the addition was completed, the reaction mixture was stirred at 50° C for 2 hours, cooled, and then poured into 250 g of ice. The aqueous reaction mixture was extracted with methylene chloride. The methylene chloride extract was washed with saturated aqueous sodium bicarbonate solution, washed with water, dried over magnesium sulfate, and evaporated to give 40 g of 5-chloro-2-thienylsulfonyl chloride.

Workup

  1. additionAfter the addition
  2. temperaturecooled
  3. extractionThe aqueous reaction mixture was extracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washwas washed with saturated aqueous sodium bicarbonate solution
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-3959aed9098e4ad699e368cbe6249dad
Source dataset
uspto-grants-1976_12
Patent number
US03996243

Reaction notes

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