Hydrogen Peroxide → 3-N-(4-chlorophenyl)-4-methoxyisophthalamide

HRID 558324Notes

Reaction equation

HRID 558324 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:9])#[N:2].OO.C(=O)([O-])[O-:24].[K+].[K+].O>CS(C)=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8](=[O:9])[C:7]2[CH:18]=[C:3]([CH:4]=[CH:5][C:6]=2[O:19][CH3:20])[C:1]([NH2:2])=[O:24])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 231414775-cyano-N-(4-chlorophenyl)-2-methoxybenzamide

Product 1

HCID 574017623-N-(4-chlorophenyl)-4-methoxyisophthalamideYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Cyano-N-(4-chlorophenyl)-2-methoxybenzamide (9.8 g) obtained in step D was dissolved in 80 mL of dimethyl sulfoxide, and the solution was cooled in a water bath. A solution prepared from 17.4 mL of a 30% aqueous solution of hydrogen peroxide and 9.5 g of potassium carbonate was added dropwise to the solution. After stirring for 1 hour, the mixture was poured into 800 mL of cold water. The precipitate formed was separated by filtration, washed with cold water, and then dried over diphosphorus pentoxide under reduced pressure to obtain 10.3 g (99%) of 3-N-(4-chlorophenyl)-4-methoxyisophthalamide.

Workup

  1. temperaturethe solution was cooled in a water bath
  2. additionwas added dropwise to the solution
  3. customThe precipitate formed
  4. customwas separated by filtration
  5. washwashed with cold water
  6. dry with materialdried over diphosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-d95412ddf2df4ea5b57956e8f016a055
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

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