Water → 1-phenyl-5-(phenylamino)-1H-pyrazole-3-carbaldehyde

HRID 2194712Notes

Reaction equation

HRID 2194712 reaction equation
[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]([CH2:19][OH:20])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.O>CS(C)=O>[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:10][C:9]([CH:19]=[O:20])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 68411083[1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanol

Product 1

HCID 866444191-phenyl-5-(phenylamino)-1H-pyrazole-3-carbaldehydeYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[1-Phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanol (318 mg) and triethylamine (1 mL) were dissolved in dimethyl sulfoxide (5 mL), and sulfur trioxide•pyridine complex (535 mg) was added at room temperature. After stirring at room temperature for 18 hr, water was added to the reaction mixture, 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 powder (yield 238 mg, yield 81%).

Workup

  1. additionsulfur trioxide•pyridine complex (535 mg) was added at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=7:1→3:1)

Sources & evidence

ORD record
ord-c5fbd86b5b104eb2aaf9c4037b0139ac
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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