Water → 1,1-dioxido-2-(4-oxo-pentyl)-1,2-benzisothiazol-3(2H)-one
Reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[Na].[OH2:14]>CN(C)C=O>[O:3]=[S:1]1(=[O:2])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:5](=[O:6])[N:4]1[CH2:9][CH2:8][CH2:7][C:12](=[O:14])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of the above ketal (3.2 gm, 15 mmol) and sodium saccharin (3.1 gm, 14 mmol) in dimethylformamide (15 mL) was heated at 170° C. for 5 hours. The cooled reaction mixture was poured into water and the crude product extracted into ethyl acetate. The dried extract was evaporated and the crude product was chromotographed on a column of silica gel eluting with a gradient of 20-40% EtOAc/hexane to give crystalline 1,1-dioxido-2-(4-oxo-pentyl)-1,2-benzisothiazol-3(2H)-one, melting point 90-93° C.
Workup
- customThe cooled reaction mixture
- extractionthe crude product extracted into ethyl acetate
- extractionThe dried extract
- customwas evaporated
Sources & evidence
- ORD record
- ord-4425c815a914467ebeb562753fda5c21
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952351
Reaction notes
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