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

HRID 1390709Notes

Reaction equation

HRID 1390709 reaction equation
[Na].[K].[C:3]1(=[O:18])[N:7]([CH2:8][S:9](O)(=[O:11])=[O:10])[C:6](=[O:13])[C:5]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:4]12.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1C=CC=CC=1>[C:3]1(=[O:18])[N:7]([CH2:8][S:9]([Cl:20])(=[O:11])=[O:10])[C:6](=[O:13])[C:5]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:4]12

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 86736311HCID 86736311, compound

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 sodium 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-3a6f5476c1d24947845fd2cdcd164c4e
Source dataset
uspto-grants-1979_02
Patent number
US04139701

Reaction notes

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