Thionyl Chloride → 5-Chlorothiophene-2-carbonyl Chloride

HRID 425233Notes

Reaction equation

HRID 425233 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([Cl:12])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 5892235-Chlorothiophene-2-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

53.6 g of 5-chlorothiophene-2-carboxylic acid (commercially available) are suspended in 344 g of toluene and heated to 80° C. At this temperature, 47.2 g of thionyl chloride are added dropwise over a period of 20 minutes, then the mixture is stirred at from 75 to 80° C. for 30 minutes and then at reflux temperature for two hours until completion of gas evolution. After cooling, the reaction mixture is concentrated to a volume of approx. 200 ml at from 30 to 35° C. and a pressure of from 40 to 48 mbar. The thus obtained solution of the acid chloride in toluene is reacted directly in the next stage.

Workup

  1. temperatureat reflux temperature for two hours until completion of gas evolution
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated to a volume of approx. 200 ml at from 30 to 35° C.
  4. customThe thus obtained solution of the acid chloride in toluene is reacted directly in the next stage

Sources & evidence

ORD record
ord-e2a35c726dad4feda65b4660503fc26a
Source dataset
uspto-grants-2012_01
Patent number
US08106192B2

Reaction notes

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