Ethanol → HCID 178509104, compound

HRID 1615715Notes

Reaction equation

HRID 1615715 reaction equation
[C:1]1([C:7]2[C:11]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([NH:20]C(=O)C)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[OH-].[Na+]>C(OCC)(=O)C.O>[C:1]1([C:7]2[C:11]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:10]([NH2:20])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 178474487HCID 178474487, compound

Product 1

HCID 178509104HCID 178509104, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-[3-phenyl-4-(2-phenylethynyl)-1H-pyrazol-5-yl]acetamide (12.5 g, 42 mmol), ethanol (100 mL) and 25% aq. NaOH solution (100 mL) was stirred and heated to 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 (5.4 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-b0062d4a807c4b718997a7ca8d6c7e0e
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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