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

HRID 650863Notes

Reaction equation

HRID 650863 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-719234d8f6524303a4168d3f12480ea5
Source dataset
uspto-grants-2001_08
Patent number
US06277791B1

Reaction notes

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