(+/-)-4-(1-Dodecenyl)-alpha-phenyl-N-(2,4,6-trimethoxyphenyl)-1H-pyrazole-1-acetamide → 2-(4-Dodecyl-pyrazol-1-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 1756952Notes

Reaction equation

HRID 1756952 reaction equation
[CH:1]([C:13]1[CH:14]=[N:15][N:16]([CH:18]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:19]([NH:21][C:22]2[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:23]=2[O:32][CH3:33])=[O:20])[CH:17]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>C1COCC1.[Pd]>[CH2:1]([C:13]1[CH:14]=[N:15][N:16]([CH:18]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:19]([NH:21][C:22]2[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[CH:26][C:27]=2[O:28][CH3:29])=[O:20])[CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 53740607(+/-)-4-(1-Dodecenyl)-alpha-phenyl-N-(2,4,6-trimethoxyphenyl)-1H-pyrazole-1-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 118004852-(4-Dodecyl-pyrazol-1-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In addition to the procedures followed in Example 122, (±)-4-(1-dodecenyl)-α-phenyl-N-(2,4,6-trimethoxyphenyl)-1H-pyrazole-1-acetamide (0.46 g, 0.9 mmol) was dissolved in 75 mL THF and 5% Pd/C (0.1 g) was added. Hydrogen gas (50 psi) was added and the reaction mixture was stirred at room temperature for 2 hours. Filtered to remove the catalyst and concentrated the filtrate to give an oil. Triturated with hexanes to give the title compound as a creamcolored solid (0.45 g, 97%); mp 77°-79° C.

Workup

  1. additionIn addition to the procedures
  2. filtrationFiltered
  3. customto remove the catalyst
  4. concentrationconcentrated the filtrate
  5. customto give an oil
  6. customTriturated with hexanes

Sources & evidence

ORD record
ord-0f367fc987c143a3bf1e59dccdcc3eae
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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