Water → [5-(3,5-dichlorophenylthio)-1-isopropyl-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

HRID 350872Notes

Reaction equation

HRID 350872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][N:13]=[C:12]([CH3:15])[C:11]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].I[CH:27]([CH3:29])[CH3:28].O>CN(C)C=O>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH:27]([CH3:29])[CH3:28])[N:13]=[C:12]([CH3:15])[C:11]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178434688HCID 178434688, compound

Product 1

HCID 22747464[5-(3,5-dichlorophenylthio)-1-isopropyl-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 75 mg of [5-(3,5-dichlorophenylthio)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone in 2 ml of dry N,N-dimethylformamide (DMF) at rt under nitrogen was treated with 12 mg of sodium hydride. The mixture was then stirred for 2 min. To the mixture was added 25 μof 2-iodopropane. The mixture was then stirred for 20 min. To the mixture was added 2mnl of water and then the mixture was extracted with ethyl acetate three times. Combined extracts were washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using diethyl ether/hexane (1:7) for the elution to give 32 mg of [5-(3,5-dichlorophenylthio)-1-isopropyl-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a colourless oil. Mass spectrum (ES) m/z 405[M+H]+.

Workup

  1. stirringThe mixture was then stirred for 20 min
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washCombined extracts were washed with brine
  4. dry with materialthen dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-11efa8e1cf2a4fd186430b15226c8eda
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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