Sodium Thiosulfate → 5-Nitro-2-thenoic acid

HRID 357734Notes

Reaction equation

HRID 357734 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].P([O-])(O)(O)=[O:12].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O.OO>[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:12])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 805915-Nitro-2-thenoic acidYield 339.1%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-Nitro-2-thiophenecarbaldehyde (7.86 g) was dissolved in acetonitrile (50 ml), and sodium dihydrogen phosphate (1.6 g) in water (20 ml) and 30% aqueous hydrogen peroxide (5.9 ml) were added. Furtherl sodium chlorite (8.0 g) in water (70 ml) was added dropwise under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours, and then sodium thiosulfate was added to remove an excess amount of hydrogen peroxide. The mixture was alkalified with 1N sodium hydroxide and extracted with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5-nitro-2-thiophenecarboxylic acid (7.83 g) as crystals.

Workup

  1. temperaturecooling
  2. customto remove an excess amount of hydrogen peroxide
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-614133e2eb7e4fb88c25c7cfd189edb8
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Reaction notes

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