Diisopropylethylamine → 3-(4-t-Butylphenyl)-1-(4-cyanophenyl)-4-ethoxycarbonyl-2-methyl-2H-pyrazol-5-one

HRID 1740073Notes

Reaction equation

HRID 1740073 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15]CC)=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH:33][CH3:34])=[CH:28][CH:27]=1)#[N:25].C(N(C(C)C)CC)(C)C>C(O)CC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:33]([CH3:34])[N:32]([C:29]3[CH:28]=[CH:27][C:26]([C:24]#[N:25])=[CH:31][CH:30]=3)[C:13](=[O:15])[C:12]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][CH:6]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 218376391-(4-Cyanophenyl)-2-methylhydrazineHCID 21837650Ethyl 3-(4-t-Butylphenyl)-3-chloro-2-ethoxycarbonyl-acrylate

Product 1

HCID 218376543-(4-t-Butylphenyl)-1-(4-cyanophenyl)-4-ethoxycarbonyl-2-methyl-2H-pyrazol-5-oneYield 40%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 73.19 g of ethyl 3-(4-t-butylphenyl)-3-chloro-2-ethoxycarbonyl-acrylate, 33.6 g of 1-(4-cyanophenyl)-2-methyl-hydrazine, 44.3 g of diisopropylethylamine and 500 ml of 1-propanol was refluxed under heating for 7 days. The reaction mixture was evaporated under reduced pressure. After addition of 1N hydrochloric acid, the resulting residue was extracted with chloroform. The extract was washed with 1N hydrochloric acid and saturated aqueous sodium chloride successively and dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was recrystallized in ethyl acetate to give 34.9 g of the title compound as colorless crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 7 days
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additionAfter addition of 1N hydrochloric acid
  5. extractionthe resulting residue was extracted with chloroform
  6. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium chloride successively
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed by evaporation
  9. customThe residue was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-cb7fff8fcea7487fb0c367ecc869e622
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

Loading…