Sodium Hydroxide → HCID 178489979, compound

HRID 1654725Notes

Reaction equation

HRID 1654725 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-(3-methoxyphenylmethyl)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 acetate) 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-a360eb6762f74165938d8b4ce34abd55
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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