Hydrogen Peroxide → HCID 135815272, compound

HRID 1977622Notes

Reaction equation

HRID 1977622 reaction equation
[OH:1]O.[OH-].[Na+].[C:5]([C:8]1[N:12]([CH3:13])[N:11]=[C:10]([CH2:14][CH2:15][CH3:16])[C:9]=1[NH:17][C:18](=O)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1)(=[O:7])[NH2:6]>O.O1CCOCC1>[OH:1][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C:18]2[NH:6][C:5](=[O:7])[C:8]3[N:12]([CH3:13])[N:11]=[C:10]([CH2:14][CH2:15][CH3:16])[C:9]=3[N:17]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 54400091HCID 54400091, compound

Product 1

HCID 135815272HCID 135815272, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Aqueous hydrogen peroxide (0.24 ml, 30% w/w, 0.0021 mol) was added to a solution of sodium hydroxide (180 mg, 0.0045 mol) in water (10 ml). A solution of N-(5-carbamoyl-1-methyl-3-propyl-1H-pyrazolyl)-2-(4-bromomethylphenyl)acetamide (400 mg, 0.001 mol) in dioxan (5 ml) was then added and the mixture stirred at 90° C. for 4 hours. On cooling, the reaction mixture was concentrated under reduced pressure, the residue dissolved in water (10 ml) and acidified to pH 5 with 1N aqueous hydrochloric acid. This solution was then extracted with dichloromethane (2×20 ml), the combined organic extracts dried (MgSO4), filtered and evaporated under reduced pressure.

Workup

  1. temperatureOn cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in water (10 ml)
  4. extractionThis solution was then extracted with dichloromethane (2×20 ml)
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-788951490477444287b4dbab801992f4
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

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