Phosphorus pentachloride → (1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methanesulfonyl chloride

HRID 839010Notes

Reaction equation

HRID 839010 reaction equation
[K+].[C:2]1(=[O:17])[N:6]([CH2:7][S:8]([O-])(=[O:10])=[O:9])[C:5](=[O:12])[C:4]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:3]12.P(Cl)(Cl)(Cl)(Cl)[Cl:19]>C1C=CC=CC=1>[C:2]1(=[O:17])[N:6]([CH2:7][S:8]([Cl:19])(=[O:10])=[O:9])[C:5](=[O:12])[C:4]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:3]12

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 88789710Phthalimidomethanesulfonic acid potassium salt

Product 1

HCID 21315191(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 41.7 g. (0.15 mol.) of phthalimidomethanesulfonic acid potassium salt in 220 ml. of dry benzene is added 22.5 g. (0.132 mol.) of phosphorus pentachloride. The reaction mixture is refluxed on a steam bath for one hour, then an additional 22.5 g. of phosphorus pentachloride is added and heating is continued for 1.5 hours. The reaction mixture is evaporated to dryness, crushed ice is added to the residue and the slurry is filtered. The product is washed with water to give phthalimidomethanesulfonyl chloride.

Workup

  1. temperatureThe reaction mixture is refluxed on a steam bath for one hour
  2. temperatureheating
  3. customThe reaction mixture is evaporated to dryness
  4. customcrushed ice
  5. additionis added to the residue
  6. filtrationthe slurry is filtered
  7. washThe product is washed with water

Sources & evidence

ORD record
ord-4e5ad735dd454d0ea14c9e3506c9c3c0
Source dataset
uspto-grants-1978_06
Patent number
US04093723

Reaction notes

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