Thionyl Chloride → 2-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

HRID 616823Notes

Reaction equation

HRID 616823 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10]([OH:13])(=O)=[O:11])=[O:4].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10]([Cl:16])(=[O:13])=[O:11])=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 214315792-(Methoxycarbonyl)thiophene-3-sulfonic acid

Product 1

HCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Procedure

7.4 g. of crude 3-sulfothiophene-2-carboxylic acid methyl ester are dissolved in 50 ml. of thionyl chloride and boiled to reflux for 16 hours. The mixture is then evaporated to dryness in vacuo and the remaining bright-yellow oil is brought to crystallization with petroleum ether. There is obtained 3-chlorosulfonylthiophene-2-carboxylic acid methyl ester.

Workup

  1. temperatureto reflux for 16 hours
  2. customThe mixture is then evaporated to dryness in vacuo
  3. customthe remaining bright-yellow oil is brought to crystallization with petroleum ether

Sources & evidence

ORD record
ord-a4e44558658d4a60b7cd5ca118e6b7a1
Source dataset
uspto-grants-1978_02
Patent number
US04076709

Reaction notes

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