Acetic Acid → 4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-1-propargyl-5-(trifluoromethyl)-1H-pyrazole

HRID 1080488Notes

Reaction equation

HRID 1080488 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=3)=[N:10][N:11]([CH2:17][C:18]#[CH:19])[C:12]=2[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.OO.[OH2:30].C(O)(=[O:33])C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:21]=[CH:22][C:23]([S:26]([CH3:27])(=[O:33])=[O:30])=[CH:24][CH:25]=3)=[N:10][N:11]([CH2:17][C:18]#[CH:19])[C:12]=2[C:13]([F:15])([F:16])[F:14])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 153802234-(4-Fluorophenyl)-3-[4-(methylthio)phenyl]-1-propargyl-5-(trifluoromethyl)pyrazole

Product 1

HCID 153409214-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-1-propargyl-5-(trifluoromethyl)-1H-pyrazoleYield 21%

Procedure

To a solution of 0.066 mmol of 4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-1-propargyl-5-(trifluoromethyl)pyrazole from step 2 in 5 mL of glacial acetic acid was added 13 mmol of 30% hydrogen peroxide. The reaction mixture was stirred at room temperature for 72 hours and poured into water. The crude product was purified by HPLC (40% ethyl acetate-hexane) followed by recrystallization from methylene chloride-hexane to give 4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-1-propargyl-5-(trifluoromethyl)-1H-pyrazole as white needles (21%): mp 158°-159.5° C.

Workup

  1. customThe crude product was purified by HPLC (40% ethyl acetate-hexane)
  2. customfollowed by recrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-e0d95f4020ed48b08e277c262639c709
Source dataset
uspto-grants-1996_12
Patent number
US05580985

Reaction notes

Loading…