Hydrazine hydrate (1:1) → HCID 66810362, compound

HRID 2390587Notes

Reaction equation

HRID 2390587 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[C:4]=1[CH:5]=[CH:6][S:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([N+:19]([O-])=O)[CH:12]=1)(=[O:9])=[O:8].O.NN>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[C:4]=1[CH:5]=[CH:6][S:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([NH2:19])[CH:12]=1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67318859HCID 67318859, compound

Product 1

HCID 66810362HCID 66810362, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,4,6-trimethoxystyryl-N-(4-methoxy-3-nitrophenyl)sulfonamide (7 mmol) (See, e.g., PCT publication WO03072063) was dissolved in ethanol (55 mL) in a round bottomed flask. Palladium catalyst (5% Pd/C, 275 mg) was added. Hydrazine hydrate (182 mmol) was then added in one portion. The resulting mixture was refluxed for 5 h and the reaction progress was monitored by TLC. When the reaction was complete, the palladium catalyst was removed by filtration and the filtrate was poured into a beaker containing ice cold water. The solution was stirred and a solid precipitate formed. The precipitated material was separated by filtration and dried in vacuum.

Workup

  1. temperatureThe resulting mixture was refluxed for 5 h
  2. customthe palladium catalyst was removed by filtration
  3. additionthe filtrate was poured into a beaker
  4. additioncontaining ice cold water
  5. customa solid precipitate formed
  6. customThe precipitated material was separated by filtration
  7. customdried in vacuum

Sources & evidence

ORD record
ord-0eb9d4306a424220803aec6b223b7398
Source dataset
uspto-grants-2012_09
Patent number
US08273787B2

Reaction notes

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