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

HRID 457260Notes

Reaction equation

HRID 457260 reaction equation
OO.[C:3]([O:6][C:7](=O)[CH3:8])(=O)C.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:23])C(C)=C)=[CH:14][C:13]=1[C:24]([F:27])([F:26])[F:25])#[N:11]>O>[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:7]2([CH3:8])[CH2:3][O:6]2)=[O:23])=[CH:14][C:13]=1[C:24]([F:25])([F:26])[F:27])#[N:11]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 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 962WaterSolvent

Procedure

10 ml of 30% aqueous hydrogen peroxide is heated to 35–40° C. 20 ml of acetic anhydride is added dropwise under cooling, so that the temperature does not exceed 40–50° C. 0.02 g of wolframic acid is added and the reaction mixture is stirred for 0.5 hours at 50–55° C. 3 grams of the amide (7) is added to the mixture portionwise and the reaction mixture is stirred for 6 hours at 50–55° C. The suspension is then cooled to 20–25° C. and poured, under stirring, into 100 ml of cold (0–5° C.) water. The suspension is stirred for 30 minutes and the solid is filtered off, washed by water and dried at 40–50° C. Yield: 2.44 g (76.5%).

Workup

  1. temperatureunder cooling, so that the temperature
  2. customdoes not exceed 40–50° C
  3. stirringthe reaction mixture is stirred for 6 hours at 50–55° C
  4. temperatureThe suspension is then cooled to 20–25° C.
  5. additionpoured
  6. stirringThe suspension is stirred for 30 minutes
  7. filtrationthe solid is filtered off
  8. washwashed by water
  9. customdried at 40–50° C

Sources & evidence

ORD record
ord-8e9cd72ad75a494c9637ec5c7b4bc594
Source dataset
uspto-grants-2007_03
Patent number
US07186854B2

Reaction notes

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