3-Methylthiophene → 3-Methylthiophene-2-sulfonyl chloride

HRID 1730067

Reaction equation

HRID 1730067 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[Cl:7][S:8](O)(=[O:10])=[O:9]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:8]([Cl:7])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 120243-MethylthiopheneHCID 24638Chlorosulfonic acid

Product 1

HCID 134257133-Methylthiophene-2-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

A 49-g (0.5 mol) sample of 3-methylthiophene was added in small portions to a cooled solution (-20° C) of 128 g (1 mol) chlorosulfonic acid in 250 cc chloroform. After the addition was completed, the reaction mixture was allowed to warm to about 25° C and then heated at reflux for 30 minutes. The reaction mixture was then diluted with ice water and neutralized with aqueous sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulfate and evaporated to give 30 g of 3-methyl-2-thienylsulfonyl chloride.

Workup

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureat reflux for 30 minutes
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-daee733669fe41d397471f0f084a84c8
Source dataset
uspto-grants-1976_11
Patent number
US03991081

Linked notes

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