2-(Methylamino)ethanol → 3-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-(N-hydroxyethyl-N-methyl-aminocarbonyl)-2-methyl-2H-pyrazol-5-one

HRID 1740089Notes

Reaction equation

HRID 1740089 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:28])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:14](=[O:19])[C:15]=2[C:16](Cl)=[O:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][NH:30][CH2:31][CH2:32][OH:33]>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:28])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:14](=[O:19])[C:15]=2[C:16]([N:30]([CH2:31][CH2:32][OH:33])[CH3:29])=[O:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 154355013-(4-t-Butylphenyl)-4-chlorocarbonyl-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one

Product 1

HCID 154355063-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-(N-hydroxyethyl-N-methyl-aminocarbonyl)-2-methyl-2H-pyrazol-5-oneYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a liquid mixture of 150 mg of 3-(4-t-butylphenyl)-4-chlorocarbonyl-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one and 3 ml of tetrahydrofuran, 72 mg of N-methylethanolamine was added at room temperature, and the resulting mixture was stirred at the same temperature for another 1 hour and then concentrated under reduced pressure. After addition of 1N hydrochloric acid, the mixture was extracted with chloroform. The extract was washed with 1N hydrochloric acid and saturated aqueous sodium chloride successively and dried over anhydrous sodium sulfate. The insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized in ethyl acetate-hexane to give 110 mg of the title compound as colorless crystals.

Workup

  1. additionwas added at room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionAfter addition of 1N hydrochloric acid
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium chloride successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insolubles were filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was recrystallized in ethyl acetate-hexane

Sources & evidence

ORD record
ord-e576bd146473447fb834e6754a6abb71
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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