Triethylamine → 1-benzyl-3-phenyl-1H-pyrazol-5-amine

HRID 34006

Reaction equation

HRID 34006 reaction equation
[C:1]([CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O)#[N:2].Cl.Cl.[CH2:14]([NH:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(O)C>[CH2:14]([N:21]1[C:1]([NH2:2])=[CH:3][C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64799BenzoylacetonitrileHCID 146540Benzylhydrazine dihydrochloride

Product 1

HCID 6847461-benzyl-3-phenyl-1H-pyrazol-5-amineYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.9 g of α-cyanoacetophenone and 3.9 g of benzyl hydrazine dihydrochloride were suspended in 50 mL of ethanol. The reaction solution was added with 6.0 ml of triethylamine at room temperature, and heated under reflux for 4 hours. The solvent was evaporated, and the residue was added with water, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:4), to afford 4.1 g of the title compound as a yellow needle powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customThe solvent was evaporated
  4. additionthe residue was added with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe residue was purified
  9. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-ab741d29a856446f992b176cf69abef4
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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