Phosphorus oxychloride → 2,3-Dioxoindoline-5-sulfonyl chloride

HRID 2186472Notes

Reaction equation

HRID 2186472 reaction equation
[N:1]1(S(O)(=O)=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[Na].C1[S:21](=[O:23])(=[O:22])CCC1.P(Cl)(Cl)([Cl:26])=O>O>[Cl:26][S:21]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[NH:1][C:2](=[O:3])[C:4]2=[O:5])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 5360545SodiumHCID 54239611HCID 54239611, compound

Product 1

HCID 159089472,3-Dioxoindoline-5-sulfonyl chlorideYield 60.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of isatinsulfonic acid, sodium salt dihydrate (10 g, 35.1 mmol) and 50 mL tetramethylene sulfone was added phosphorus oxychloride (16.5 mL, 177 mmol). The resulting mixture was heated at 60° C. for 3 hours. Cool the mixture to 0° C. and cautiously add 120 mL of water. Filter the resulting green solid and wash with water. Dissolve the solid in 100 mL EtOAc and wash three times with 50 mL of water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow solid. The solid was recrystallized from EtOAc/Hexanes to give the title compound as an orange solid (5.2 g, 60.5%). ES (−) MS m/e=344 (M−H).

Workup

  1. temperatureCool the mixture to 0° C.
  2. filtrationFilter the resulting green solid
  3. washwash with water
  4. dissolutionDissolve the solid in 100 mL EtOAc
  5. washwash three times with 50 mL of water
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a yellow solid
  10. customThe solid was recrystallized from EtOAc/Hexanes

Sources & evidence

ORD record
ord-3e36d1f7fa5f41bd9dfc8df84f254546
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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