Ethanol → HCID 178434676, compound

HRID 588575Notes

Reaction equation

HRID 588575 reaction equation
[CH3:1][C:2]1[C:6]([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:15]C(=O)C)[NH:4][N:3]=1.C(O)C.[OH-].[Na+]>C(OCC)(=O)C.O>[CH3:1][C:2]1[C:6]([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH2:15])[NH:4][N:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 178474490HCID 178474490, compound

Product 1

HCID 178434676HCID 178434676, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(3-methyl-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide (15 g, 63 mmol), ethanol (50 mL) and 25% aq. NaOH solution (50 mL) was stirred at 90° C. for 1 h and cooled to room temperature. The reaction mixture was diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried (phase separator cartridge) and concentrated in vacuo. Diethyl ether was added to the residue and the solid was collected by filtration, washed with diethyl ether and dried in vacuo to provide the title compound as a solid (3.3 g).

Workup

  1. temperaturecooled to room temperature
  2. washThe organic phase was washed with water and brine
  3. customdried (phase separator cartridge)
  4. concentrationconcentrated in vacuo
  5. additionDiethyl ether was added to the residue
  6. filtrationthe solid was collected by filtration
  7. washwashed with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c7595f56d7714a6187add08fa49d4658
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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