Saccharin → Pseudosaccharin chloride

HRID 1154712Notes

Reaction equation

HRID 1154712 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[NH:4]1)(=[O:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:14]>>[Cl:14][C:5]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[S:1](=[O:3])(=[O:2])[N:4]=1

Participants

3

Reactant 2

HCID 5143SaccharinHCID 24819Phosphorus pentachloride

Product 1

HCID 64783Pseudosaccharin chlorideYield 28%

Procedure

Following the procedure of Stephen et al., J. Chem. Soc., 1957, 490-92, 1 mol of saccharin (1,2-benzisothiazol-3(2H)-one 1,1-dioxide) is heated with 1.1 mol phosphorus pentachloride at 170° C. for 1.5 hours. Phosphorus oxychloride is removed at 60°/30 mm and the yellow crystalline residue of ψ-saccharin chloride and o-cyanobenzene sulfonyl chloride is treated with ether in which the latter is soluble. The sparingly soluble ψ-saccharin chloride in a yield of 28% is collected and crystallized from ether as white needles, m.p. 132°-137° C.

Workup

  1. customPhosphorus oxychloride is removed at 60°/30 mm
  2. additionthe yellow crystalline residue of ψ-saccharin chloride and o-cyanobenzene sulfonyl chloride is treated with ether in which the latter
  3. customThe sparingly soluble ψ-saccharin chloride in a yield of 28% is collected
  4. customcrystallized from ether as white needles, m.p. 132°-137° C.

Sources & evidence

ORD record
ord-5a8cc0b7876f49e19b3eac65d8451727
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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