Potassium hydroxy sulfite → HCID 86741656, compound

HRID 653463Notes

Reaction equation

HRID 653463 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH2:10][CH2:9]S[CH:7]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:6]=12.OO[S:20]([O-:22])=[O:21].[K+]>CO.O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH2:10][CH2:9][S:20](=[O:22])(=[O:21])[CH:7]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:6]=12

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86741654HCID 86741654, compound

Product 1

HCID 86741656HCID 86741656, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5,6-dihydro-4-(2-hydroxyethoxy)thieno[2,3-b]thiopyran-2-sulfonamide (1.0 g, 0.0034 mole) in CH3OH (20 ml) was added dropwise a solution of OXONE® (3.15 g, 0.005 mole) in water (20 ml). The mixture was stirred at ambient temperature overnight and then filtered, washing the filter cake thoroughly with CH3OH. Methanol was stripped from the filtrate in vacuo and the residue was extracted repeatedly with ethyl acetate. Evaporation of the dried extract left the crude product as a yellow gum that was purified by column chromatography on silica gel (75 g, 230-400 mesh). The product was eluted with 90 CHCl3 :10CH3OH:1H2O. Evaporation of the eluate left a colorless glass (0.8 g) that was triturated with ether, collected, dried in vacuo, and recrystallized from water. The yield of white crystalline product, m.p. 159°-164° C., was 430 mg (39%).

Workup

  1. filtrationfiltered
  2. washwashing the filter cake thoroughly with CH3OH
  3. extractionthe residue was extracted repeatedly with ethyl acetate
  4. customEvaporation of the dried
  5. extractionextract
  6. waitleft the crude product as a yellow gum that
  7. customwas purified by column chromatography on silica gel (75 g, 230-400 mesh)
  8. washThe product was eluted with 90 CHCl3
  9. customEvaporation of the eluate
  10. waitleft a colorless glass (0.8 g) that
  11. customwas triturated with ether
  12. customcollected
  13. customdried in vacuo
  14. customrecrystallized from water

Sources & evidence

ORD record
ord-f2b78df1cb56413aa3687f7c68b13d6f
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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