4,5-Dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine → 1-(4-Fluorophenyl)-5-[4-(methylthio)phenyl]-3-pyrazolamine

HRID 654775Notes

Reaction equation

HRID 654775 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)[CH2:11][C:10]([NH2:21])=[N:9]2)=[CH:4][CH:3]=1>ClCCl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([NH2:21])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 104945294,5-Dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine

Product 1

HCID 107565811-(4-Fluorophenyl)-5-[4-(methylthio)phenyl]-3-pyrazolamineYield 64.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,5-dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine (1 g) and manganese (IV) oxide (1.16 g) in dichloromethane (100 ml) was stirred at ambient temperature for 2 hours. The insoluble was filtered and the filtrate was concentrated to dryness. The residue (1 g) was purified by column chromatography on silica gel (16 g) eluting with a mixture of chloroform and ethyl acetate (5:1 to give a pale brown powder of 1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine (0.64 g).

Workup

  1. filtrationThe insoluble was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue (1 g) was purified by column chromatography on silica gel (16 g)
  4. washeluting with a mixture of chloroform and ethyl acetate (5:1

Sources & evidence

ORD record
ord-c1edf38799ef42efae8da5373a03e824
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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