Hydrogen Peroxide → 2,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid amide

HRID 2240849Notes

Reaction equation

HRID 2240849 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[CH3:7][C:8]1([CH3:19])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]1[C:17]#[N:18].OO>CS(C)=O.[Cl-].[Na+].O>[CH3:7][C:8]1([CH3:19])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]1[C:17]([NH2:18])=[O:2]

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide3×HCID 11430Potassium CarbonateHCID 134298982,2-Dimethyl-3-phenylcyclopropanecarbonitrile

Product 1

HCID 576527872,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid amide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Potassium carbonate (467 mg) was added to a solution of 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile (3/1 cis/trans mixture, 4 g, 23.4 mmol) in DMSO (7 mL). The resulting mixture was cooled to 0° C. and an aqueous solution of hydrogen peroxide (30%, 2.8 mL) was added. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. A second aliquot of aqueous solution of hydrogen peroxide (30%, 2.8 mL) was added and the resulting mixture was stirred for 24 hours. A third aliquot of aqueous solution of hydrogen peroxide (30%, 3.0 mL) was added and the resulting mixture was stirred for 3 days. The reaction mixture was poured into brine and extracted with ethyl ether. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (0% to 65% of EtOAc in hexane) to give 2.66 of 2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid amide (2/1 trans/cis mixture), together with 1.125 g of starting material.

Workup

  1. temperatureto warm up to room temperature
  2. stirringthe resulting mixture was stirred for 24 hours
  3. stirringthe resulting mixture was stirred for 3 days
  4. extractionextracted with ethyl ether
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (0% to 65% of EtOAc in hexane)

Sources & evidence

ORD record
ord-a84b4d5c25714a378f072e7ac14052ee
Source dataset
uspto-grants-2010_05
Patent number
US07723391B2

Reaction notes

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