Saccharin → Pseudosaccharin chloride

HRID 2056071Notes

Reaction equation

HRID 2056071 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-538fc1e3254d4e499cd2ceaba89c5235
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

Loading…