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Acetic Anhydride → N-[[4-[2-(3-pyridinyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]phenyl]sulfonyl]acetamide

HRID 2414790
Notes
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Reaction equation

HRID 2414790 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH:2]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26](=[O:28])[CH3:27])(=[O:23])=[O:24])=[CH:18][CH:17]=3)[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[N:11]=2)[CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 97993874-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamide

Product 1

HCID 12016145N-[[4-[2-(3-pyridinyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]phenyl]sulfonyl]acetamideYield 90%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent

Procedure

A mixture of 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide (0.5 g, 1.36 mmol), acetic anhydride (0.42 g, 4.1 mmol), 4-dimethylaminopyridine (DMAP) (0.083 g, 0.68 mmol) and triethylamine (0.17 g, 1.6 mmol) was stirred at room temperature for 16 hours. The reaction mixture was diluted with 50 mL of water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was recrystallized from ethyl acetate and hexane to afford 0.5 g (90%) of N-[[4-[2-(3-pyridinyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]phenyl]sulfonyl]acetamide as a colorless solid: mp (DSC): 244-246 _C. Anal. Calc'd. for C17H13F3N4O3S: C, 49.76; H, 3.19; N, 13.65; S, 7.81. Found: C, 49.66; H, 3.06; N, 13.53; S, 8.11.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. customthe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-73396c8f8f154b52ae6b4d86c50eb771
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06815460B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes