Acetic Acid → N-((4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)sulfonyl)acetamide

HRID 29042

Reaction equation

HRID 29042 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)=[CH:4][CH:3]=1.[C:27](O)(=[O:29])[CH3:28]>C(Cl)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH:22][C:27](=[O:29])[CH3:28])(=[O:21])=[O:20])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:24])([F:26])[F:25])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 2662Celecoxib

Product 1

HCID 10364984N-((4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)sulfonyl)acetamide

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent2×

Procedure

4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (0.60 g, 1.57 mmol) was heated in 2 mL acetyl chloride and 2 mL acetic acid at reflux for 2 h. An additional 2 mL acetyl chloride was added and the mixture was heated to reflux for an additional 5 h. The mixture was cooled and concentrated. Recrystallization from ether/hexane furnished the product as a white solid: Anal. Calc'd for C19H16N3O3SF3: C, 53.90; H, 3.81; N, 9.92; S, 7.57. Found: C, 54.04; H, 3.80; N, 9.93; S, 7.66.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for an additional 5 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-3b48363a2245414d8dd818042418c8ad
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Linked notes

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