Hydrogen Peroxide → 5-(5-bromo-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxamide

HRID 522129Notes

Reaction equation

HRID 522129 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=[C:12]([C:21]#[N:22])[CH:11]=1)=[O:8].C([O-])([O-])=[O:26].[K+].[K+].OO>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=[C:12]([C:21]([NH2:22])=[O:26])[CH:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 1184561205-bromo-2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)benzamide

Product 1

HCID 1184560435-(5-bromo-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-bromo-2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)benzamide (Preparation 15, 500 mg, 1.24 mmol) in DMSO (5 mL) was added K2CO3 (340 mg, 2.48 mmol) followed by H2O2 (50% by weight, aqueous solution, 1.69 mL, 24.9 mmol). The reaction was stirred at room temperature for 3 hours. The reaction was quenched by the addition of saturated aqueous KHSO4 solution (5 mL) followed by water (15 mL) and EtOAc (40 mL). The mixture was filtered and separated. The organic layer was washed with brine (40 mL), dried over MgSO4, and concentrated in vacuo. The residue was slurried in water and filtered to afford the title compound (457 mg, 88%).

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous KHSO4 solution (5 mL)
  2. filtrationThe mixture was filtered
  3. customseparated
  4. washThe organic layer was washed with brine (40 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered

Sources & evidence

ORD record
ord-3e2fa4cbd83542a9b3758571a2e04b8c
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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