Hydrogen Peroxide → HCID 59597182, compound

HRID 218665Notes

Reaction equation

HRID 218665 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][CH2:9][CH:8]2[C:13]([N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=1)[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)=[O:14])#[N:2].[OH-:35].[Na+].OO>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][CH2:9][CH:8]2[C:13]([N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=1)[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)=[O:14])(=[O:35])[NH2:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 59597229HCID 59597229, compound

Product 1

HCID 59597182HCID 59597182, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-Cyano-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamide (0.9 g) was dissolved in acetone (12.8 mL), and 1 mol/L-aqueous sodium hydroxide solution (6.4 mL) and 30% aqueous hydrogen peroxide (3.8 mL) were added. The mixture was heated under reflux for 2 hr. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 8-carbamoyl-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamide (21 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-181a80cedb0448729cfb75284c09c2dd
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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