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

HRID 1057519Notes

Reaction equation

HRID 1057519 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. The mixture was cooled to 0° C. and 120 mL of water was cautiously added. The resulting green solid was filtered and washed with water. The solid was dissolved in 100 mL EtOAc and washed thrice 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. temperatureThe mixture was cooled to 0° C.
  2. filtrationThe resulting green solid was filtered
  3. washwashed with water
  4. dissolutionThe solid was dissolved in 100 mL EtOAc
  5. washwashed thrice 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-14a3912941414f64bec69fd17bb5e346
Source dataset
uspto-grants-2003_02
Patent number
US06514992B1

Reaction notes

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