Water → 2,3-Dioxoindoline-5-sulfonyl chloride
Reaction equation
O.[Na+].[N:3]1(S([O-])(=O)=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[C:4]1=[O:5].P(Cl)(Cl)([Cl:20])=O.O.C1[S:28](=[O:30])(=[O:29])CCC1>>[O:5]=[C:4]1[C:6](=[O:7])[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([S:28]([Cl:20])(=[O:30])=[O:29])[CH:9]=2)[NH:3]1Participants
Conditions
- Temperature
- 60 °C
Procedure
A mixture of isatinsulfonic acid sodium salt hydrate (10.00 g, 39.7 mmol ) and phosphorous oxychloride (18.5 mL, 199 mmol, 5 eq) in tetramethylene sulfone (50 mL) was heated at 60° C. for 3 hours under a dry N2 atmosphere. The reaction was cooled in an ice bath to 0 C. and water was cautiously added drop-wise, keeping the internal temperature below 6° C. The resulting green solid was collected by filtration and was washed well with water. The solid was dissolved in ethyl acetate (200 mL) and washed again with water (3×50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude product in 85% yield. The solid was recrystallized from ethyl acetate: hexanes with hot filtration to give the title compound (5.81 g, 66% yield). NMR (400 MHz, DMSO-d6): consistent.
Workup
- temperatureThe reaction was cooled in an ice bath to 0 C
- customthe internal temperature below 6° C
- filtrationThe resulting green solid was collected by filtration
- washwas washed well with water
- dissolutionThe solid was dissolved in ethyl acetate (200 mL)
- washwashed again with water (3×50 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product in 85% yield
- customThe solid was recrystallized from ethyl acetate
- filtrationhexanes with hot filtration
Sources & evidence
- ORD record
- ord-ea23949bb1214ba4b26c38a06394ae01
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07256198B2
Reaction notes
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