HCID 14372118, compound → HCID 14372119, compound

HRID 1383020Notes

Reaction equation

HRID 1383020 reaction equation
[S:1]([C:5]1[O:13][C:12]2[CH:11]=[C:10]([CH2:14][S:15][CH2:16][CH2:17][CH3:18])[N:9]=[CH:8][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].I([O-])(=O)(=O)=[O:20].[Na+].I([O-])(=O)=O.[Na+]>CO.O>[S:1]([C:5]1[O:13][C:12]2[CH:11]=[C:10]([CH2:14][S:15]([CH2:16][CH2:17][CH3:18])=[O:20])[N:9]=[CH:8][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 14372118HCID 14372118, compoundHCID 23667635Sodium periodateHCID 23675764Sodium Iodate

Product 1

HCID 14372119HCID 14372119, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-sulfamoyl-6-(propylthiomethyl)furo[3,2-c]pyridine (913 mg, 3.19 mmol) in methanol (23 mL) and water (8 mL) was added sodium metaperiodate (906 mg, 4.24 mmol). This mixture was stirred for 4 hours as sodium iodate precipitated from the solution. This precipitate was filtered off and the methanol was evaporated. Sodium chloride was added to the residual aqueous solution and this was exhaustively extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was triturated with diethyl ether/methylene chloride to give 820 mg of product. This material was crystallized from a large volume of ethyl acetate to give pure product (470 mg, 49% yield), mp: 179°-180.5° C. (dec).

Workup

  1. customprecipitated from the solution
  2. filtrationThis precipitate was filtered off
  3. customthe methanol was evaporated
  4. additionSodium chloride was added to the residual aqueous solution
  5. extractionthis was exhaustively extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was triturated with diethyl ether/methylene chloride

Sources & evidence

ORD record
ord-206d2d69c49e4acb93f0eae6837be1cc
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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