Hydrogen Peroxide → 4-Chloro-3,5-bis(trifluoromethyl)benzamide

HRID 1487007Notes

Reaction equation

HRID 1487007 reaction equation
[Cl:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].C([O-])([O-])=[O:19].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[C:3]([C:14]([F:15])([F:16])[F:17])=[CH:4][C:5]([C:6]([NH2:7])=[O:19])=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 226251933,5-Bis(trifluoromethyl)-4-chlorobenzonitrile

Product 1

HCID 867303704-Chloro-3,5-bis(trifluoromethyl)benzamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Chloro-3,5-bis(trifluoromethyl)benzonitrile (1 g, 1.0 eq.) was dissolved in DMSO (10 mL). K2CO3 (0.55 g, 1.1 eq.) and H2O2 (1 mL) were added to the reaction mixture and stirred at room temperature for 2-3 h, then poured into ice water (20 mL). The precipitate formed was collected by filtration and washed with petroleum ether to afford 1.0 g of crude product (90% yield), which was used without further purification in the next step.

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with petroleum ether

Sources & evidence

ORD record
ord-00da5095a4d148659b177c1fa89bca13
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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