Hydrogen Peroxide → 2-Chloro-4-(4-formyl-phenoxy)-benzamide

HRID 492345Notes

Reaction equation

HRID 492345 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=[O:20].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]([NH2:5])=[O:20]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 597300142-Chloro-4-(4-formylphenoxy)benzonitrile

Product 1

HCID 597301722-Chloro-4-(4-formyl-phenoxy)-benzamideYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-chloro-4-(4-formylphenoxy)benzonitrile (1.0 equiv) in DMSO (0.2 M solution) was treated with K2CO3 (0.5 equiv) and 33% H2O2. After 12 h, the reaction mixture was poured into H2O and extracted with ethyl acetate. The combined organic layers were washed twice with water and brine. After drying the extracts over magnesium sulfate and evaporation under vacuum, the crude product was purified by silica gel chromatography using the appropriate eluent (typically mixtures of hexanes/ethyl acetate) to afford the title compound as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed twice with water and brine
  3. customAfter drying the extracts
  4. customover magnesium sulfate and evaporation under vacuum
  5. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fbf5ff41a6fc464195e2fafbb9b2f913
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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