Thionyl Chloride → Pseudosaccharin chloride

HRID 2419998Notes

Reaction equation

HRID 2419998 reaction equation
[S:1]1(=[O:11])(=[O:10])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1.S(Cl)([Cl:14])=O.O1CCOCC1>CN(C)C=O>[Cl:14][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1](=[O:10])(=[O:11])[N:2]=1

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 312751,4-DioxaneHCID 130862071H-1lambda~6~,2-Benzothiazole-1,1-dione

Product 1

HCID 64783Pseudosaccharin chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

100 g (545 mM) of benzisothiazole-1,1-dioxide 100 ml. of thionyl chloride, 4 ml. of dimethylformamide (catalyst) and 400 ml. of dioxane are refluxed overnight. Thionyl chloride (50 ml.) and dimethylformamide (1 ml.) are added to the reaction mixture which is again refluxed overnight. The reaction mixture is evaporated to dryness and the residue recrystallized from toluene to obtain 73.4 g of 3-chloro-1,2-benzisothiazole-1,1-dioxide, m.p. 140°-145°.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-04b913fb6bf6417b9da2b894a1c6d41a
Source dataset
uspto-grants-1978_08
Patent number
US04108860

Reaction notes

Loading…