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

HRID 904340Notes

Reaction equation

HRID 904340 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-sulphothiophene-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 crystallisation with petroleum ether. There is obtained 3-chlorosulphonylthiophene-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 crystallisation with petroleum ether

Sources & evidence

ORD record
ord-9fc0c518c0f34b04b9c3816c8a4e4658
Source dataset
uspto-grants-1980_10
Patent number
US04230873

Reaction notes

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