Dimethylformamide → 3-Chloro-4-fluoro-1,2-benzisothiazole 1,1-dioxide

HRID 470594Notes

Reaction equation

HRID 470594 reaction equation
[F:1][C:2]1[C:7]2[C:8](=O)[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O.CN(C=O)C>O1CCOCC1>[Cl:16][C:8]1[C:7]2[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=2[S:10](=[O:12])(=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl Chloride2×HCID 142574924-Fluoro-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

Product 1

HCID 674127093-Chloro-4-fluoro-1,2-benzisothiazole 1,1-dioxideYield 93.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.1 g of 4-fluoro-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (EP291851 A2 19881123), 2 g of thionyl chloride and a catalytic amount of DMF in 6 ml of dioxane are heated under reflux for 18 hours. Then additional 2 g of thionyl chloride are added and the mixture is heated for 8 hours. The mixture is concentrated and 1.12 g of a crude solid is obtained.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperaturethe mixture is heated for 8 hours
  3. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-2d13b2caa01748399485e41bbe020612
Source dataset
uspto-grants-2014_01
Patent number
US08629284B2

Reaction notes

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