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

HRID 653518Notes

Reaction equation

HRID 653518 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:15]([NH2:18])(=[O:17])=[O:16])[C:5]2[O:10][S:9](=[O:12])(=[O:11])[CH:8]([CH3:13])[CH2:7][C:6]=2[CH:14]=1.C([O-])(=O)C.[Na+]>[Pd].O1CCCC1>[O:12]=[S:9]1(=[O:11])[CH:8]([CH3:13])[CH2:7][C:6]2[CH:14]=[CH:2][CH:3]=[C:4]([S:15]([NH2:18])(=[O:16])=[O:17])[C:5]=2[O:10]1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 201950286-Bromo-3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,2 g of 6-bromo-3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide are hydrogenated in the presence of 0.7 g of sodium acetate and 0.3 g of 5% palladium on carbon catalyst at 20° C. and 1 bar in 45 ml of tetrahydrofurane. The catalyst is removed, the solvent evaporated, the residue taken up with a mixture of water and ethyl acetate. The organic phase is separated, washed with a saturated aqueous solution of sodium chloride, dried and concentrated. The residue is crystallised from acetonitrile, affording 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide with a melting point of 204°-205° C.

Workup

  1. customThe catalyst is removed
  2. customthe solvent evaporated
  3. additionthe residue taken up with a mixture of water and ethyl acetate
  4. customThe organic phase is separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is crystallised from acetonitrile

Sources & evidence

ORD record
ord-6e067bc784ea4a8fbd58544f1e4a0794
Source dataset
uspto-grants-1987_06
Patent number
US04677212

Reaction notes

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