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

HRID 40755Notes

Reaction equation

HRID 40755 reaction equation
[K].[C:2]1(=[O:19])[N:6]([CH2:7][CH2:8][CH2:9][S:10]([O-])(=[O:12])=[O:11])[C:5](=[O:14])[C:4]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:3]12.P(Cl)(Cl)(Cl)(Cl)[Cl:21]>C1(C)C=CC=CC=1>[C:2]1(=[O:19])[N:6]([CH2:7][CH2:8][CH2:9][S:10]([Cl:21])(=[O:12])=[O:11])[C:5](=[O:14])[C:4]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:3]12

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 86647898HCID 86647898, compound

Product 1

HCID 154532703-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propane-1-sulfonyl chlorideYield 100.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium-3-phthalimidopropane-1-sulfonate (6.0 g) was suspended in dry toluene (25 ml) under a nitrogen atmosphere and heated to reflux. Then 4.11 g of PCl5 was added in portions and the mixture was heated at reflux for 60 minutes. A second portion of 4.11 g of PCl5 was added and heating was continued for 90 minutes. The reaction mixture was evaporated to dryness and crushed ice was added to the residual solid. When the ice had just molten, the solid was filtered off and dried in vacuo to yield 5.64 g (87%) of a solid. 1H-NMR (CDCl3) δ (ppm) 7.88-7.81 (m, 2H), 7.78-7.71 (m, 2H), 3.87 (t, J=6.5 Hz, 2H), 3.77-3.69 (m, 2H), 2.48-2.34 (m, 2H).

Workup

  1. temperatureheated to reflux
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 60 minutes
  4. temperatureheating
  5. customThe reaction mixture was evaporated to dryness
  6. customcrushed ice
  7. additionwas added to the residual solid
  8. filtrationthe solid was filtered off
  9. customdried in vacuo

Sources & evidence

ORD record
ord-06895965c37a4c6da20c94fc3d092c91
Source dataset
uspto-grants-2013_09
Patent number
US08530486B2

Reaction notes

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