Water → 4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazole

HRID 375656Notes

Reaction equation

HRID 375656 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19](=O)[C:20]([F:23])([F:22])[F:21])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[NH2:25][NH2:26].O>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=3)=[N:25][NH:26][C:19]=2[C:20]([F:23])([F:22])[F:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 193560322-(4-Fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butanedione

Product 1

HCID 153802214-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazoleYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Crude 2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butanedione (Example 3, Step 2) (1.0 g) was reacted with anhydrous hydrazine (0.13 g) in glacial acetic acid. The mixture was held at 80°-110° C. for 18 hours and poured into water. The resulting solid precipitate was filtered, purified by HPLC and recrystallized from methylene chloride-hexane to give 4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazole as a solid (0.88 g, 89%): mp 189°-190° C.

Workup

  1. filtrationThe resulting solid precipitate was filtered
  2. custompurified by HPLC
  3. customrecrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-029b310ea967468ebc456452f6cea466
Source dataset
uspto-grants-1996_01
Patent number
US05486534

Reaction notes

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