Thionyl Chloride → Benzo[b]thiophene-2-carbonyl Chloride

HRID 1814704Notes

Reaction equation

HRID 1814704 reaction equation
S(Cl)([Cl:3])=O.[S:5]1[C:9]([C:10](O)=[O:11])=[CH:8][C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]1=2>CN(C=O)C.C1(C)C=CC=CC=1>[S:5]1[C:9]([C:10]([Cl:3])=[O:11])=[CH:8][C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]1=2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 95864Benzo(b)thiophene-2-carboxylic acid

Product 1

HCID 142384Benzo[b]thiophene-2-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

The Benzo[b]thiophene-2-carbonyl chloride was prepared by adding toluene (2 mL), DMF (2 drops) and thionyl chloride (50 μL) to benzo[b]thiophene-2-carboxylic acid. Heating the mixture to reflux for 5 hours followed by removal of the solvent afforded the crude product, which was used without further purification.

Workup

  1. temperatureHeating the mixture
  2. temperatureto reflux for 5 hours
  3. customfollowed by removal of the solvent

Sources & evidence

ORD record
ord-de49ac937bd349d3bfc1f0422d2e77db
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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