HCID 178515138, compound → 5-Aminosaccharin

HRID 266440Notes

Reaction equation

HRID 266440 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[S:9](=[O:11])(=[O:10])[N:8](C(SC1NN=NN=1)C1C=CC=CC=1)[C:7]2=[O:28])([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[S:9](=[O:11])(=[O:10])[NH:8][C:7]2=[O:28]

Participants

4

Reactant 1

HCID 178515138HCID 178515138, compound

Product 1

HCID 647885-Aminosaccharin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Nitro-2-(1-phenyl-1H-tetrazol-5-ylthiomethyl)saccharin (4 g, 9.56 mmol) (Example 11) was dissolved in THF (250 ml) and placed in a Parr shaker bottle. Two spatulas of 10% palladium-on-charcoal catalyst were added under nitrogen, and the mixture was shaken under hydrogen (55 psi) for 2.5 days. The reaction mixture was filtered through Celite diatomaceous earth and filtrate mixed with water and extracted with MDC. The organic layer was dried (Na2SO4), freed of solvent under vacuum, and the resultant yellow foam was sonicated with warm ethanol, cooled and filtered. The desired 5-aminosaccharin derivative, 0.5 g, was isolated as a cream colored solid. FDMS: m/e 388 (M+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite diatomaceous earth and filtrate
  2. additionmixed with water
  3. extractionextracted with MDC
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe resultant yellow foam was sonicated with warm ethanol
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-48fa7fd2f51a4f38adfcf97f319b4834
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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