Methanol → 1-(4-Fluorophenyl)-3-(methoxyacetyl)-5-[4-(methylsulfonyl)phenyl]pyrazole

HRID 654787Notes

Reaction equation

HRID 654787 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[N:6]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[N:5]=1)(=[O:3])[CH3:2].[OH2:26].O.O.[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.Cl(O)(=O)(=O)=O.[CH3:47]O>O1CCOCC1>[F:25][C:22]1[CH:21]=[CH:20][C:19]([N:6]2[C:7]([C:9]3[CH:10]=[CH:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=3)=[CH:8][C:4]([C:1](=[O:3])[CH2:2][O:26][CH3:47])=[N:5]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24247Perchloric AcidHCID 11270721Nitric acid,thallium(3+) salt, trihydrate (9CI)HCID 19886267HCID 19886267, compound

Product 1

HCID 198862571-(4-Fluorophenyl)-3-(methoxyacetyl)-5-[4-(methylsulfonyl)phenyl]pyrazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-acetyl-1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (1.1 g), thallium (III) nitrate trihydrate (1.6 g) and perchloric acid (70%; 3.3 ml) in methanol (16 ml) and dioxane (8 ml) was stirred at ambient temperature overnight. The insoluble was filtered, and the filtrate was diluted with chloroform, washed with water, dried and concentrated. The residue (1.6 g) was purified by column chromatography on silica gel (100 g) eluting with a mixture of toluene and ethyl acetate (2:1) to give pale brown crystals of 1-(4-fluorophenyl)-3-(methoxyacetyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (0.13 g).

Workup

  1. filtrationThe insoluble was filtered
  2. additionthe filtrate was diluted with chloroform
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue (1.6 g) was purified by column chromatography on silica gel (100 g)
  7. washeluting with a mixture of toluene and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-54574f63f4534a73b2a6c04759e8bd39
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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