Hydrogen Peroxide → HCID 44236487, compound

HRID 1500246Notes

Reaction equation

HRID 1500246 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:12][C:13]#[N:14])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.OO.C(=O)([O-])[O-:18].[K+].[K+].O>CS(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:12][C:13]([NH2:14])=[O:18])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 58155388HCID 58155388, compound

Product 1

HCID 44236487HCID 44236487, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [1-(4-methoxyphenyl)cyclopropyl]acetonitrile (60.4 mmol) in DMSO (75 mL) is treated with H2O2 (50% w/w) (434 mmol) and potassium carbonate (121 mmol) at zero degrees Celsius. The reaction mixture is stirred at room temperature over the weekend. The reaction mixture is transferred into a separatory funnel using water (100 mL) and CH2Cl2 (200 mL). The mixture is equilibrated and the CH2Cl2 layer is removed. The aqueous layer is extracted two additional times with CH2Cl2 (2×300 mL). The combined CH2Cl2 extracts are washed 5 consecutive times with water (5×200 mL) followed by a brine (500 mL) wash, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, which affords 2-[1-(4-methoxyphenyl)-cyclopropyl]-acetamide.

Workup

  1. customThe reaction mixture is transferred into a separatory funnel
  2. customthe CH2Cl2 layer is removed
  3. extractionThe aqueous layer is extracted two additional times with CH2Cl2 (2×300 mL)
  4. washThe combined CH2Cl2 extracts are washed 5 consecutive times with water (5×200 mL)
  5. washwash
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure, which

Sources & evidence

ORD record
ord-dcab67a51f0f42b19156cb2d9ace5220
Source dataset
uspto-grants-2015_12
Patent number
US09206143B2

Reaction notes

Loading…