Hydrogen Peroxide → 1-[3-[4-(2-Methylimidazol-1-yl)benzyloxy]phenyl]cyclobutane-1-carboxamide

HRID 1108091Notes

Reaction equation

HRID 1108091 reaction equation
[C:1]([C:3]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[CH:24][N:23]=[C:22]4[CH3:26])=[CH:17][CH:16]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2].OO.C(=O)([O-])[O-:30].[K+].[K+].O>CS(C)=O>[CH3:26][C:22]1[N:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:9]3[CH:8]=[C:7]([C:3]4([C:1]([NH2:2])=[O:30])[CH2:6][CH2:5][CH2:4]4)[CH:12]=[CH:11][CH:10]=3)=[CH:16][CH:17]=2)[CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 187863611-Cyano-1-[3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-cyclobutane

Product 1

HCID 153921311-[3-[4-(2-Methylimidazol-1-yl)benzyloxy]phenyl]cyclobutane-1-carboxamideYield 203.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-cyano-1-[3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-cyclobutane (2.90 g, 8.4 mmol) in DMSO (5 ml) cooled to 0° C. was added 30% H2O2 (2.0 ml) and potassium carbonate (0.4 g). The mixture was allowed to warm to room temperature and stirred overnight, and then stirred for 6 hrs at 60° C. Water (100 ml) was added and the mixture extracted with ethyl acetate (100 ml×3). The combined organic layers were extracted with 2N HCl (100 ml×2) and the aqueous layer washed with ethyl acetate (100 ml×3). The aqueous acidic layer was basified to pH=9 with 5N NaOH (150 ml) and extracted with ethyl acetate (100 ml×3). The combined organic extracts were washed with water (100 ml), brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford crude product as white solid. Recrystallization from ethyl acetate gave 2.13 g (70%) of the titled compound as a white solid.

Workup

  1. stirringstirred for 6 hrs at 60° C
  2. extractionthe mixture extracted with ethyl acetate (100 ml×3)
  3. extractionThe combined organic layers were extracted with 2N HCl (100 ml×2)
  4. washthe aqueous layer washed with ethyl acetate (100 ml×3)
  5. extractionextracted with ethyl acetate (100 ml×3)
  6. washThe combined organic extracts were washed with water (100 ml), brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto afford crude product as white solid
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8d9fc55803f540b6976e0632ab2de987
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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