Hydrogen Peroxide → HCID 18760011, compound

HRID 432663Notes

Reaction equation

HRID 432663 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=O)[CH2:12][CH:13]=O)=[CH:7][CH:6]=1.OO>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][N:3]=[N:2][C:15]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24654Hydrazine hydrate (1:1)HCID 18759987HCID 18759987, compound

Product 1

HCID 18760011HCID 18760011, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.8 mP, 16.5 mmol) was added to a solution of 3-(4-chlorophenyl)-4-[4-(methylsulfonyl)phenyl]-4-oxo-butyraldehyde (4.5 g, 12.8 mmol) in ethanol (100 ml), followed by stirring at room temperature for 1 hour. Hydrogen peroxide solution 31% (6 ml) was added to the reaction mixture, and the resulting mixture was stirred at 60° C. for 18 hours. The mixture was concentrated under reduced pressure and the residue was separated and purified by chromatography on a silica gel column [silica gel 70 g, chloroform/methanol (50/1)], whereby the title compound was obtained as a pale yellow amorphous solid (2.60 g, 58.8%).

Workup

  1. stirringthe resulting mixture was stirred at 60° C. for 18 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was separated
  4. custompurified by chromatography on a silica gel column [silica gel 70 g, chloroform/methanol (50/1)], whereby the title compound

Sources & evidence

ORD record
ord-05e0335a302f416cada679175a8523ac
Source dataset
uspto-grants-2003_12
Patent number
US06664256B1

Reaction notes

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