HCID 13911591, compound → HCID 13911602, compound

HRID 653454Notes

Reaction equation

HRID 653454 reaction equation
OO[S:3]([O-:5])=[O:4].[K+].[OH:7][CH:8]1[C:13]([CH3:15])([CH3:14])[CH2:12]S[C:10]2[S:16][C:17]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:18][C:9]1=2>O.CO>[OH:7][CH:8]1[C:13]([CH3:12])([CH3:14])[CH2:15][S:3](=[O:5])(=[O:4])[C:10]2[S:16][C:17]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:18][C:9]1=2

Participants

5

Reactant 2

HCID 13911591HCID 13911591, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 13911602HCID 13911602, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of OXONE® (2.71 g, 0.0044 m) in water (15 ml) was added to a solution of 5,6-dihydro-4-hydroxy-5,5-dimethyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide (0.90 g, 0.0032 m) in methanol (15 ml) over 10 minutes and the mixture was stirred at ambient temperature for 2.5 hours. The mixture was filtered, the solid was washed with methanol, and the combined filtrate and washings were concentrated in vacuo below 65° C. to remove methanol. The aqueous suspension was extracted with ethyl acetate (3×50 ml), the combined extracts were washed with water, dried over sodium sulfate and evaporated under reduced pressure to give 0.91 g (91%) of crude product which was purified by chromatography on silica gel, eluting with 10% methanol-chloroform.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with methanol
  3. concentrationthe combined filtrate and washings were concentrated in vacuo below 65° C.
  4. customto remove methanol
  5. extractionThe aqueous suspension was extracted with ethyl acetate (3×50 ml)
  6. washthe combined extracts were washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ddff9b39f59347229e86be4af2081451
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

Loading…