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p-Toluenesulfonic acid monohydrate → HCID 15908406, Verbindung

HRID 497191
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 497191
O[C:2]1([C:28]([F:31])([F:30])[F:29])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:18]=2)=[N:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][S:13]([C:10]1[CH:9]=[CH:8][C:7]([N:5]2[CH:6]=[C:2]([C:28]([F:30])([F:29])[F:31])[N:3]=[C:4]2[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:14])=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22316766HCID 22316766, Verbindung

Produkt 1

HCID 15908406HCID 15908406, VerbindungAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-[4-(2-thienyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole (0.345 g, 0.74 mmol) and p-toluenesulfonic acid monohydrate (0.035 g) in toluene (40 mL) was heated to reflux for 7 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude residue was redissolved in CH2Cl2 (50 mL) and the whole washed with water, aqueous NaHCO3 (30 mL), and brine. After dried over Na2SO4, and concentration in vacuo. The crude mixture was purified by flash chromatography eluting with hexane/ethyl acetate (2/1). The resulting solid was recrystallized from ethyl acetate-hexane to give the title compound (0.212 g, 63.9% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was redissolved in CH2Cl2 (50 mL)
  6. washthe whole washed with water, aqueous NaHCO3 (30 mL), and brine
  7. dry with materialAfter dried over Na2SO4, and concentration in vacuo
  8. customThe crude mixture was purified by flash chromatography
  9. washeluting with hexane/ethyl acetate (2/1)
  10. customThe resulting solid was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-11c4fb6dac574a1fad22dbe283571814
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06949536B2

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