HCID 178515138, compound → HCID 178507257, compound

HRID 266456Notes

Reaction equation

HRID 266456 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]([CH:15]([S:22][C:23]1[NH:27][N:26]=[N:25][N:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]2=[O:28])([O-])=O>[Ni].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[S:9](=[O:11])(=[O:10])[N:8]([CH:15]([S:22][C:23]1[NH:27][N:26]=[N:25][N:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:7]2=[O:28]

Participants

4

Reactant 1

HCID 178515138HCID 178515138, compound

Product 1

HCID 178507257HCID 178507257, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

5-Nitro-2-(1-phenyl-1H-tetrazol-5-ylthiomethyl)saccharin (1 g, 0.0024 mol) was reduced over 3 spatulas of Rainey nickel (washed with THF prior to use) in 150 ml of THF under 50 psi hydrogen pressure. When reduction was complete (in about 5 hours) the reaction mixture was filtered, the filter pad washed with THF, and the filtrate evaporated to dryness to give a pale yellow, cloudy oil which was taken into hot ethanol and filtered. On cooling, the product separated and was collected to give 0.4 g (43%) of 5-amino-2-(1-phenyl-1H-tetrazol-5-ylthiomethyl)saccharin as yellow crystals.

Workup

  1. washwashed with THF
  2. custom(in about 5 hours)
  3. filtrationwas filtered
  4. washthe filter pad washed with THF
  5. customthe filtrate evaporated to dryness
  6. customto give a pale yellow, cloudy oil which
  7. filtrationfiltered
  8. temperatureOn cooling
  9. customthe product separated
  10. customwas collected

Sources & evidence

ORD record
ord-76c2e90cbb454b918e2b8ccf98455184
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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