Sodium Hydroxide → HCID 178424829, compound

HRID 1654723Notes

Reaction equation

HRID 1654723 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]([CH3:20])[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]([CH3:20])[CH:15]=3)=[CH:11][CH:12]=2)=[CH:5][NH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20076639HCID 20076639, compound

Product 1

HCID 178424829HCID 178424829, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-amino-2-carbamoyl-4-[4-(3-methylphenylmethyl) phenyl]pyrazole (2.0 g) in methanol (20 ml) was added 5N sodium hydroxide solution (10 ml), and the mixture was refluxed for 4 hours. Methanol was distilled away under reduced pressure. To the residue was added water (100 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 chloroform:methanol=10:1) to give a mixture containing the title compound. This mixture Was used in the subsequent reaction without isolation.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. distillationMethanol was distilled away under reduced pressure
  3. additionTo the residue was added water (100 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
  10. customto give a mixture

Sources & evidence

ORD record
ord-bcb22db0cddd440cad7119711f22c004
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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