Aniline → 2-[4-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-pyrazol-1-yl]-N-phenyl-acetamide

HRID 1292233Notes

Reaction equation

HRID 1292233 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([C:34]3[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=3)=[N:21][N:22]([CH2:28][C:29](OCC)=[O:30])[C:23]=2[C:24]([F:27])([F:26])[F:25])=[CH:15][CH:14]=1>C(Cl)Cl>[C:2]1([NH:1][C:29](=[O:30])[CH2:28][N:22]2[C:23]([C:24]([F:27])([F:25])[F:26])=[C:19]([C:16]3[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=3)[C:20]([C:34]3[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=3)=[N:21]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10227082ethyl [4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetateHCID 16682925Trimethylaluminum

Product 1

HCID 101186862-[4-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-pyrazol-1-yl]-N-phenyl-acetamideYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Aniline (0.07 g, 0.75 mmol) was added to a methylene chloride solution of trimethyl aluminum (0.38 mL, 0.75 mmol, 2.0M in hexanes) at 25° C. under nitrogen. After gas evolution had ceased (approx. 30 minutes), ethyl [4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetate (Example 8) (0.25 g, 0.5 mmol) was added and the mixture stirred for 24 hours at 25° C. The reaction was quenched with dilute aqueous HCl and extracted with two portions ethyl acetate and the extracts washed with brine, dried over MgSO4 and concentrated in vacuo. Recrystallization from chloroform/acetone gave N-phenyl-[4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetamide as a white crystalline solid (0.18 g, 68% yield). Elemental analysis for C25H19N3F4SO3 Calc'd: C, 58.02, H, 3.70, N, 8.12, S, 6.20. Found: C, 57.48, H, 3.78, N, 8.03, S, 6.46.

Workup

  1. additionwas added
  2. customThe reaction was quenched with dilute aqueous HCl
  3. extractionextracted with two portions ethyl acetate
  4. washthe extracts washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from chloroform/acetone

Sources & evidence

ORD record
ord-a2e5d76447ba486dbacba9120cb54091
Source dataset
uspto-grants-1998_05
Patent number
US05756530

Reaction notes

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