Hydrochloric Acid → HCID 178438916, compound

HRID 439804Notes

Reaction equation

HRID 439804 reaction equation
[NH2:1][C:2]1[N:3](C(=O)N)[N:4]=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH3:14])=[CH:9][CH:8]=1.[OH-].[Na+].O.Cl>CO>[NH2:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([CH3:15])[CH3:14])=[CH:11][CH:12]=2)=[CH:5][NH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22408120HCID 22408120, compound

Product 1

HCID 178438916HCID 178438916, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-amino-2-carbamoyl-4-[4-(2-phenylpropan-2-yl)phenyl]pyrazole (1.5 g) in methanol (20 ml) was added 5N sodium hydroxide solution (2 l), and the mixture was refluxed. To the mixture was added water (50 ml) under ice-cooling, and the mixture was neutralized (pH 7 to 8) with 10% hydrochloric acid solution, and was extracted with chloroform. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous potassium carbonate, and the solvent was distilled away under reduced pressure. The residue was separated and purified by using a silica-gel column chromatography (chloroform:methanol=1:3) to give the title compound (980 mg, 75.5%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturecooling
  3. extractionwas extracted with chloroform
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous potassium carbonate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe residue was separated
  8. custompurified

Sources & evidence

ORD record
ord-01ed0954f73b411b960f892a850a9ac9
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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