Tetrahydrofuran → 3,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

HRID 746289Notes

Reaction equation

HRID 746289 reaction equation
[O:1]=[S:2]1(=[O:17])[CH:7]=[C:6](C)[C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13]([NH2:16])(=[O:15])=[O:14])[C:4]=2[O:3]1.[H][H].O1CCC[CH2:21]1>[Pd]>[O:17]=[S:2]1(=[O:1])[CH:7]([CH3:21])[CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13]([NH2:16])(=[O:14])=[O:15])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 233107972,2-Dioxo-4-methyl-1,2-benzoxathiin-8-ylsulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 135920753,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

10.0 g of 2,2-dioxo-4-methyl-1,2-benzoxathiin-8-ylsulfonamide are dissolved in 200 ml of tetrahydrofuran and the solution is hydrogenated with hydrogen for 21/2 hours, in the presence of 2.0 g of 5% palladium on carbon catalyst, under a pressure of 4 bar and at a temperature of 40° C. After removal of the catalyst the solution is concentrated and the residue is crystallised from 120 ml of 70% aqueous ethanol, affording 9.0 g of 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of m.p. 185°-186° C.

Workup

  1. custom2 hours
  2. customat a temperature of 40° C
  3. customAfter removal of the catalyst the solution
  4. concentrationis concentrated
  5. customthe residue is crystallised from 120 ml of 70% aqueous ethanol

Sources & evidence

ORD record
ord-57b59547b6ce4528962a24976cde5eb4
Source dataset
uspto-grants-1986_07
Patent number
US04603211

Reaction notes

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