Sulfuric Acid → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 448820

Reaction equation

HRID 448820 reaction equation
[O-]S(OOS([O-])(=O)=O)(=O)=O.[K+].[K+].S(=O)(=O)(O)O.CN(C)C=O.[Br:23][C:24]1[CH2:28][CH:27]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[C:39](=[O:46])[NH:40][CH:41]([CH:43]2[CH2:45][CH2:44]2)[CH3:42])=[O:30])[N:26]([C:47]2[C:52]([Cl:53])=[CH:51][CH:50]=[CH:49][N:48]=2)[N:25]=1>C(OCC)(=O)C.O>[Br:23][C:24]1[CH:28]=[C:27]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[C:39](=[O:46])[NH:40][CH:41]([CH:43]2[CH2:45][CH2:44]2)[CH3:42])=[O:30])[N:26]([C:47]2[C:52]([Cl:53])=[CH:51][CH:50]=[CH:49][N:48]=2)[N:25]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 24412Potassium PersulfateHCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Product 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamideYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.24 g of potassium peroxodisulfate and 0.02 g of sulfuric acid were added to 3 ml of an N,N-dimethylformamide solution containing 0.10 g of 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide, followed by heating and refluxing. After 1.5 hours, the reaction liquid was left to cool and introduced into 10 ml of water, and then ethyl acetate was added, followed by extraction. The organic layer (the ethyl acetate layer) was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/2) to obtain 0.09 g of the desired product (melting point: 231-233° C.).

Workup

  1. temperatureby heating
  2. temperaturerefluxing
  3. customthe reaction liquid
  4. waitwas left
  5. temperatureto cool
  6. extractionfollowed by extraction
  7. washThe organic layer (the ethyl acetate layer) was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/2)

Sources & evidence

ORD record
ord-5b2021305ef24e90aa308a488e79064a
Source dataset
uspto-grants-2013_07
Patent number
US08481744B2

Linked notes

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