Thionyl Chloride → 3,4-Dichloro-5-isothiazolecarbonyl chloride

HRID 478131Notes

Reaction equation

HRID 478131 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:10]([Cl:11])=[C:9]([C:12]([OH:14])=O)[S:8][N:7]=1>CN(C)C=O>[Cl:5][C:6]1[C:10]([Cl:11])=[C:9]([C:12]([Cl:3])=[O:14])[S:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 498373,4-Dichloro-5-isothiazolecarboxylic acid

Product 1

HCID 109768863,4-Dichloro-5-isothiazolecarbonyl chlorideYield 125.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

At room temperature, 146 g (1.23 mol) of thionyl chloride are added dropwise with stirring over a period of 5 minutes to 8.92 g (0.045 mol) of 3,4-dichloro-isothiazole-5-carboxylic acid. Four drops of dimethylformamide are then added and the reaction mixture is heated under reflux for one hour. The reaction mixture is subsequently cooled to room temperature and concentrated under reduced pressure. In this manner, 12.19 g of 3,4-dichloro-isothiazole-5-carbonyl chloride are obtained in the form of an orange oil.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for one hour
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e77c88e15e0648339fb7ab32203be537
Source dataset
uspto-grants-2003_11
Patent number
US06642181B2

Reaction notes

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