Hydrogen Peroxide → 3-Chloro-4-(4-formylphenoxy)benzamide

HRID 130953Notes

Reaction equation

HRID 130953 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)[C:5]#[N:6].C(=O)([O-])[O-:20].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)[C:5]([NH2:6])=[O:20]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 568514253-Chloro-4-(4-formylphenoxy)benzonitrile

Product 1

HCID 568514263-Chloro-4-(4-formylphenoxy)benzamideYield 166.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Cool a solution of 3-chloro-4-(4-formyl-phenoxy)-benzonitrile (1.57 g, 6.10 mmol) in dimethylsulfoxide (50 mL) to 0° C. Add potassium carbonate (0.42 g, 3.05 mmol) followed by 30% aqueous hydrogen peroxide (1.83 mL, 6.10 mmol). Remove the cooling bath and let stir at rt for 3 hrs. Pour into water (100 mL) and after trituration, filter the solid formed to obtain the product (1.40 g, 84%). 1H NMR (DMSO-d6) 9.93 (s, 1H), 8.12 (d, J=1.2 Hz, 1H), 8.10 (bs, 1H), 7.95-7.90 (m, 3H), 7.53 (bs, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.13 (d, J=8.6 Hz, 2H).

Workup

  1. customRemove the cooling bath
  2. additionPour into water (100 mL)
  3. filtrationafter trituration, filter the solid
  4. customformed

Sources & evidence

ORD record
ord-cc0a54336af446ff80cef0e79b674b83
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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