Pyridine → N-(4-acetylphenyl)-4-(trifluoromethoxy)benzenesulfonamide

HRID 130480Notes

Reaction equation

HRID 130480 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:17][C:18]([F:31])([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(OCC)(=O)C>C1COCC1>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:26]([C:23]2[CH:22]=[CH:21][C:20]([O:19][C:18]([F:17])([F:30])[F:31])=[CH:25][CH:24]=2)(=[O:28])=[O:27])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7468p-AminoacetophenoneHCID 8857Ethyl AcetateHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chloride

Product 1

HCID 8190013N-(4-acetylphenyl)-4-(trifluoromethoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-Amino acetophenone (0.375 g, 2.78 mmol) was dissolved in THF (5 ml) before pyridine (0.674 ml, 8.34 mmol) was added, leaving a yellow solution. 4-trifluoromethoxy benzenesulfonylchloride (0.871 g, 3.34 mmol) was then added dropwise with stirring. After strirring for 2 h, THF and pyridine were removed. The desired sulfonamide (0.848 g, 2.36 mmol, 85%) was recrystallized from ethyl acetate and hexanes. 1H-NMR: (400 MHz, CDCl3) 7.89 (m, 4H), 7.29 (d, 1H), 7.16 (d, 2H), 6.88 (s, 1H), 2.55 (s, 3H). LC-MS (ES+): 360 [MH]+ m/e.

Workup

  1. additionwas added
  2. customleaving a yellow solution
  3. customTHF and pyridine were removed

Sources & evidence

ORD record
ord-07186870e59b4ec69280a86056a5f567
Source dataset
uspto-grants-2008_06
Patent number
US07381749B2

Reaction notes

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