Saccharin → Pseudosaccharin chloride

HRID 897994Notes

Reaction equation

HRID 897994 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]>C(OCC)C>[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

4

Reactant 2

HCID 5143SaccharinHCID 24819Phosphorus pentachloride

Product 1

HCID 64783Pseudosaccharin chlorideYield 33.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Saccharin (10.0 g, 0.0546 mol) and phosphorus pentachloride (12.6 g, 0.060 mol) were heated at 170° C. for 1.5 hours. The reaction mixture was cooled to ambient temperature and suspended in diethyl ether (200 mL). The precipitate was collected by filtration, thoroughly washed with diethyl ether and dried to yield 3-chloro-1H-1λ6-benzo[d]isothiazole-1,1-dione (3.7 g, 0.0184 mol) as a white solid which was used without further purification.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washthoroughly washed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-555c4339f6f94d6cb3cfbabf2098721d
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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