Triethylamine → 3-Methyl-8-sulfamoyl-2,2-dioxo-1,2-benzoxathiine

HRID 746288Notes

Reaction equation

HRID 746288 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])[C:8]([CH3:13])=[CH:7][C:6]=2[CH:14]=1.[H][H].C(N(CC)CC)C>O1CCCC1.[Pd]>[O:12]=[S:9]1(=[O:11])[C:8]([CH3:13])=[CH: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

6

Reactant 3

HCID 8471TriethylamineHCID 135920736-Bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 135920743-Methyl-8-sulfamoyl-2,2-dioxo-1,2-benzoxathiineYield 75.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

120 g of 6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide are dissolved in 2.4 liters of tetrahydrofuran and the solution is hydrogenated with hydrogen for 40 minutes, in the presence of 41.3 g of triethylamine and 12.0 g of 5% palladium on carbon catalyst, under normal pressure and in the temperature range from 20° to 25° C. The mixture is filtered, the filtrate is concentrated, and the residue is taken up in 1300 ml of hot 90% aqueous ethanol. The insoluble constituents are separated and the solution is cooled to 0° C. The precipitate is separated and dried, affording 70 g of 2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of m.p. 204°-205° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe insoluble constituents are separated
  4. customThe precipitate is separated
  5. customdried

Sources & evidence

ORD record
ord-892b0c62711c44559d00a55d318f0e3e
Source dataset
uspto-grants-1986_07
Patent number
US04603211

Reaction notes

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