Ethanol → Celecoxib

HRID 49688

Reaction equation

HRID 49688 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1C.Cl.[S:17]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1)(=[O:20])(=[O:19])[NH2:18].[CH2:29](O)C>O>[CH3:29][C:9]1[CH:8]=[CH:7][C:6]([C:5]2[N:27]([C:24]3[CH:23]=[CH:22][C:21]([S:17]([NH2:18])(=[O:20])=[O:19])=[CH:26][CH:25]=3)[N:28]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 223952941,1,1-Trifluoro-4-(o-tolyl)but-3-yn-2-one

Product 1

HCID 2662Celecoxib

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1,1,1-trifluoro-4-(methylphenyl)-3-butyn-2-one (3, 10 mmol) in ethanol (100 mL) is refluxed with 4-sulfamylphenyl hydrazine hydrochloride (4, 12 mmol) for 4 h. The reaction mixture is cooled and diluted with water. The precipitated crude 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide is filtered and recrystallized.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe precipitated crude 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
  3. filtrationis filtered
  4. customrecrystallized

Sources & evidence

ORD record
ord-bd38d68fc917443f9c7154a1c559e206
Source dataset
uspto-grants-2004_03
Patent number
US06706927B2

Linked notes

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