Hydrogen Peroxide → N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide

HRID 505594Notes

Reaction equation

HRID 505594 reaction equation
[CH3:1][C:2](=[CH2:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=1)=[O:4].C(O)(C(F)(F)F)=[O:20].OO>C(Cl)Cl>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3]([C:2]2([CH3:1])[CH2:18][O:20]2)=[O:4])=[CH:7][C:8]=1[C:14]([F:15])([F:16])[F:17])#[N:13]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 11149469N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide

Product 1

HCID 10149314N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-N-(4-cyano-3-trifluoromethyl-phenyl)-acrylamide (1.35 g, 5.0 mmol) in CH2Cl2 (15 ml) was treated by TFA (3.0 ml) at 0° C. To the reaction mixture was then added H2O2 (30%, 1.0 ml, 10.0 mmol) dropwise. The reaction mixture was stirred overnight and quenched by NaHCO3, then extracted by ethyl acetate. The organic layers were combined and dried over Na2SO4, concentrated and purified by silica gel column using hexanes:ethyl acetate 4:1 as eluent to yield the title compound as a white solid.

Workup

  1. customquenched by NaHCO3
  2. extractionextracted by ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column

Sources & evidence

ORD record
ord-639f7d50858642e3a3b2af3eb4f8fbc9
Source dataset
uspto-grants-2010_08
Patent number
US07781473B2

Reaction notes

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