Water → HCID 86644418, compound

HRID 2194711Notes

Reaction equation

HRID 2194711 reaction equation
[CH:1]([C:3]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1)=[O:2].[C:24](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[CH:1]([C:3]1[CH:7]=[C:6]([N:8]([CH3:24])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1)=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86644417HCID 86644417, compound

Product 1

HCID 86644418HCID 86644418, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-formyl-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (331 mg) in N,N-dimethylformamide (5 mL) were added potassium carbonate (182 mg) and iodomethane (215 mg) at room temperature. After stirring at room temperature for 1 hr, the mixture was further stirred at 80° C. for 1 hr, and allowed to cool to room temperature. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=7:1→3:1) to give the title compound as a pale-yellow amorphous (yield 297 mg, yield 86%).

Workup

  1. stirringthe mixture was further stirred at 80° C. for 1 hr
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=7:1→3:1)

Sources & evidence

ORD record
ord-024a57c969e44e14b637982fc714801c
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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