Phosphorus pentachloride → 2-Phthalimidoethanesulfonyl chloride

HRID 582793Notes

Reaction equation

HRID 582793 reaction equation
[K+].[C:2]1(=[O:18])[N:6]([CH2:7][CH2:8][S:9]([O-])(=[O:11])=[O:10])[C:5](=[O:13])[C:4]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:3]12.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1(C)C=CC=CC=1>[C:2]1(=[O:18])[N:6]([CH2:7][CH2:8][S:9]([Cl:20])(=[O:11])=[O:10])[C:5](=[O:13])[C:4]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:3]12

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 22960477Potassium 2-phthalimidoethanesulfonate (1:1)

Product 1

HCID 3087392-Phthalimidoethanesulfonyl chlorideYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

60 g of the compound obtained in step A in 300 ml of toluene are heated to reflux for 1 hour in the presence of 30.7 g of phosphorus pentachloride. 30.7 g of phosphorus pentachloride are added again and refluxing is maintained for 90 minutes. 280 g of ice are added to the reaction medium, the mixture is stirred, and the insoluble matter is filtered off and then washed with ice-cold water. The residue is dried over P2O5 and then recrystallized in dichloroethane to obtain 32 g of the expected product, m.p.=160° C.

Workup

  1. temperaturerefluxing
  2. temperatureis maintained for 90 minutes
  3. filtrationthe insoluble matter is filtered off
  4. washwashed with ice-cold water
  5. dry with materialThe residue is dried over P2O5
  6. customrecrystallized in dichloroethane

Sources & evidence

ORD record
ord-e0170aca037f45e2b2106b7e8c1c509e
Source dataset
uspto-grants-1999_07
Patent number
US05925661

Reaction notes

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