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

HRID 571266Notes

Reaction equation

HRID 571266 reaction equation
O.O.[O:3]=[C:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:14]([O-:17])(=O)=[O:15])[CH:10]=2)[NH:5]1.[Na+].O=P(Cl)(Cl)[Cl:21].S1(CCCC1)(=O)=O>O>[O:3]=[C:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:14]([Cl:21])(=[O:17])=[O:15])[CH:10]=2)[NH:5]1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 51003678Isatin-5-sulfonic acid sodium salt dihydrate

Product 1

HCID 159089472,3-Dioxoindoline-5-sulfonyl chlorideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of sodium 2,3-dioxoindoline-5-sulfonate dihydrate (5.0 g, 17.53 mmol) and POCl3 (8.17 ml, 88 mmol) in sulfolane (25 ml, 264 mmol) was heated at 60° C. for 3 hours. The solution was cooled to 0° C. and water (60 ml) was added drop wise; the green precipitate was filtered and washed with a small amount of water. The solid was dissolved in ethyl acetate and washed three times with water; the organic phase was then dried over sodium sulfate and evaporated to give a crude solid that was purified by crystallization from hexane/ethyl acetate 1:1 to give 2,3-dioxoindoline-5-sulfonyl chloride (3.52 g, 14.33 mmol, 82% yield).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. filtrationthe green precipitate was filtered
  3. washwashed with a small amount of water
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. washwashed three times with water
  6. dry with materialthe organic phase was then dried over sodium sulfate
  7. customevaporated
  8. customto give a crude solid that
  9. customwas purified by crystallization from hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-82bea943c6264cb68bb06a22af1cd06c
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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