Sodium Hydroxide → HCID 178489979, compound

HRID 439800Notes

Reaction equation

HRID 439800 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]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)=[CH:11][CH:12]=2)=[CH:5][NH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22408169HCID 22408169, compound

Product 1

HCID 178489979HCID 178489979, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-amino-2-carbamoyl-4-[4-(3methoxyphenylmethyl)phenyl]pyrazole (4.1 g) in methanol (50 ml) was added 5N sodium hydroxide solution (20 ml), and the mixture was refluxed for 30 minutes. Methanol was distilled away under reduced pressure. To the residue was added water (150 ml), and the mixture was neutralized (pH 7 to 8) with conc. hydrochloric acid, and extracted with chloroform. The extract was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was separated and purified by using a silica-gel column chromatography (ethyl acetate:n-hexane=1:1, followed by ethyl acetat) to give the title compound (1.8 g).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. distillationMethanol was distilled away under reduced pressure
  3. additionTo the residue was added water (150 ml)
  4. extractionextracted with chloroform
  5. washThe extract was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was separated
  9. custompurified

Sources & evidence

ORD record
ord-b81d7a576c8e41e5ad83a17372697467
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

Loading…