Water → 2-Fluoro-4-[4-methyl-2-[4-(4-thiazolyl)phenyl]-1H-imidazol-1-yl]benzenesulfonamide

HRID 396842Notes

Reaction equation

HRID 396842 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[C:22]([Si](C)(C)C)[S:23][CH:24]=3)=[CH:16][CH:15]=2)[CH:5]=[CH:4][C:3]=1[S:29]([NH2:32])(=[O:31])=[O:30].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[CH:22][S:23][CH:24]=3)=[CH:16][CH:15]=2)[CH:5]=[CH:4][C:3]=1[S:29]([NH2:32])(=[O:30])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 223170002-Fluoro-4-[4-methyl-2-[4-(2-trimethylsilylthiazol-4-yl)phenyl)-1H-imidazol-1-yl]benzenesulfonamide

Product 1

HCID 223166432-Fluoro-4-[4-methyl-2-[4-(4-thiazolyl)phenyl]-1H-imidazol-1-yl]benzenesulfonamideYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-fluoro-4-[4-methyl-2-[4-(2-trimethylsilylthiazol-4-yl)phenyl]-1H-imidazol-1-yl]benzenesulfonamide (crude, 0.634 mmol) in THF (3 mL) was added tetrabutylammonium fluoride (0.95 mL, 1.0 M solution in THF, 0.95 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 30 minutes. The reaction mixture was added water (20 mL) and extracted with ethyl acetate (20 mL×3). The organic layer was washed with water and brine. After dried over MgSO4 and concentration in vacuo. The crude mixture was purified by flash chromatography eluting with hexane/ethyl acetate (1/3). The resulting solid was recrystallized from ethyl acetate-hexane to give the title compound (0.116 g, 44.1% yield, via 2 steps).

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. washThe organic layer was washed with water and brine
  3. dry with materialAfter dried over MgSO4 and concentration in vacuo
  4. customThe crude mixture was purified by flash chromatography
  5. washeluting with hexane/ethyl acetate (1/3)
  6. customThe resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a770d4ccfc794303b84026d4b35ce73c
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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