p-Toluenesulfonic acid monohydrate → 2-Benzo[1,3]dioxol-5-yl-1-(4-methanesulfonyl-phenyl)-4-trifluoromethyl-1H-imidazole

HRID 1166333

Reaktionsgleichung

Reaktionsgleichung von HRID 1166333
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C:14](O)([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:21]2[CH:29]=[CH:28][C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:21]2[CH:29]=[CH:28][C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 105986165-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole

Produkt 1

HCID 107876982-Benzo[1,3]dioxol-5-yl-1-(4-methanesulfonyl-phenyl)-4-trifluoromethyl-1H-imidazoleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]-1,3-benzodioxole from Step 2 (1.26 g, 2.9 mmol) and p-toluenesulfonic acid monohydrate (200 mg) in toluene (50 mL) was heated to reflux for 72 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude residue was redissolved in methylene chloride and washed with water, aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration in vacuo, the crude mixture (1.34 g) was purified by chromatography on silica gel using toluene/ethyl acetate 1/1 to give pure 5-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]-1,3-benzodioxole (940 mg, 80%) as a white solid: mp (DSC) 165° C. Anal Calc'd. for C18H13N2SO4F3: C, 52.68, H, 3.19, N, 6.83. Found: C, 53.05, H, 3.19, N, 6.65.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 72 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was redissolved in methylene chloride
  6. washwashed with water, aqueous sodium bicarbonate and brine
  7. customAfter drying
  8. filtration(Na2SO4), filtration and concentration in vacuo
  9. customthe crude mixture (1.34 g) was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-65fa7f2a2ba14f0499749955afbba73c
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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