m-Chloroperbenzoic acid → N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide

HRID 457259Notes

Reaction equation

HRID 457259 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16])#[N:2].ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:11]2([CH3:13])[CH2:12][O:27]2)=[O:14])=[CH:5][C:4]=1[C:15]([F:17])([F:16])[F:18])#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic 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

460 mg of the amide (7) from the Example 1 was dissolved in 30 ml of dichloromethane. 560 mg of m-chloroperbenzoic acid (purity 70–75%) was added. The reaction mixture was stirred overnight at reflux. The reaction was monitored with HPLC. The reaction mixture was washed successively with 2×20 ml of a sodium sulfite solution, 2×20 ml of saturated aqueous NaHCO3 and 20 ml of brine. The organic layer was dried (Na2SO4), filtrated and evaporated under reduced pressure yielding the epoxide (5A) as yellow solid material. Isolated yield: 400 mg (82%). 1H- and 13C-NMR confirmed the expected structure. HPLC: 96% purity.

Workup

  1. temperatureat reflux
  2. washThe reaction mixture was washed successively with 2×20 ml of a sodium sulfite solution, 2×20 ml of saturated aqueous NaHCO3 and 20 ml of brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltrated
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-21cdb9439eeb4a488357142f6552a73b
Source dataset
uspto-grants-2007_03
Patent number
US07186854B2

Reaction notes

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