Sodium Thiosulfate → HCID 22731410, compound

HRID 1356719Notes

Reaction equation

HRID 1356719 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]([C:27]1[O:28][C:29]([CH2:36][OH:37])=[CH:30][C:31]=1[S:32]([NH2:35])(=[O:34])=[O:33])([CH3:26])([CH3:25])[CH3:24].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[C:23]([C:27]1[O:28][C:29]([CH:36]=[O:37])=[CH:30][C:31]=1[S:32]([NH2:35])(=[O:34])=[O:33])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 22731423HCID 22731423, compound

Product 1

HCID 22731410HCID 22731410, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one (0.60 g) was added to a solution of 2-tert-butyl-5-hydroxymethyl-furan-3-sulfonamide (0.30 g) in methylene chloride (10 ml), followed by stirring for 25 min. The reaction mixture was mixed with a 20% aqueous sodium thiosulfate solution, extracted with methylene chloride. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated under reduced pressure to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1) to give the titled compound (267 mg, 90%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-bbf62b7f3c1b4d1b9f8a7186d960d0cd
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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