Potassium Carbonate → [5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

HRID 47613

Reaction equation

HRID 47613 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+].[Cl:31][C:32]1[CH:33]=[C:34]([SH:39])[CH:35]=[C:36]([Cl:38])[CH:37]=1>CN(C)C=O>[Cl:31][C:32]1[CH:33]=[C:34]([S:39][C:2]2[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[N:5]=[C:4]([CH3:16])[C:3]=2[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:35]=[C:36]([Cl:38])[CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 27360963,5-Dichlorobenzenethiol3×HCID 22747458[5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Product 1

HCID 22747490[5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanoneYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 170 mg of [5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone in 10 ml of N,N-dimethylformamide was treated with 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was heated at 100° C. for 4 h. The mixture was treated with a further 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was then heated at 50° C. for 64 h. The mixture was treated with a further 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was then heated at 100° C. for 2 h. The solvent was removed under reduced pressure and residue partitioned between dichloromethane/water, washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified via flash chromatography on silica gel using diethyl ether/petroleum ether (1:4 to 1:3) to give 140 mg of [5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a colourless oil. Mass spectrum (ES) m/z 483[M+H]+.

Workup

  1. temperatureThe mixture was then heated at 50° C. for 64 h
  2. temperatureThe mixture was then heated at 100° C. for 2 h
  3. customThe solvent was removed under reduced pressure and residue
  4. custompartitioned between dichloromethane/water
  5. washwashed with brine
  6. dry with materialthen dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified via flash chromatography on silica gel

Sources & evidence

ORD record
ord-c0e6a679e6c5490d93739aaac5a73549
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Linked notes

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