Saccharin → Pseudosaccharin chloride

HRID 2172829Notes

Reaction equation

HRID 2172829 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][S:10](=[O:12])(=[O:11])[C:4]2=[CH:3][CH:2]=1)=O.S(Cl)([Cl:15])=O.CN(C)C=O>O1CCOCC1>[Cl:15][C:7]1[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[S:10](=[O:12])(=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 5143SaccharinHCID 6228DimethylformamideHCID 24386Thionyl Chloride

Product 1

HCID 64783Pseudosaccharin chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of o-sulfobenzimide (5.00 g) in dioxane (20 ml) were added thionyl chloride (7.5 ml) and dimethylformamide (0.25 ml), and the mixture was stirred overnight at 110° C. The reaction mixture was concentrated under reduced pressure, and to the residue was added toluene (20 ml) to give 3-chloro-1,2-benzisothiazole 1,1-dioxide (3.77 g) as crystals. The obtained 3-chloro-1,2-benzisothiazole 1,1-dioxide (3.77 g) was dissolved in dioxane (20 ml), 3-aminorhodanine (2.77 g) was added thereto, and the mixture was stirred at 110° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and to the residue was added chloroform (20 ml) to give 3-[(4-oxo-2-thioxothiazolidin-3-yl)amino]-1,2-benzisothiazole 1,1-dioxide (3.56 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added toluene (20 ml)

Sources & evidence

ORD record
ord-63ab9d8cedb643ec8b9a5d3812ccacb7
Source dataset
uspto-grants-2015_06
Patent number
US09056862B2

Reaction notes

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