p-Toluenesulfonic acid monohydrate → 1-(4-Methanesulfonyl-phenyl)-2-thiophen-3-yl-4-trifluoromethyl-1H-imidazole

HRID 52362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52362
O[C:2]1([C:22]([F:25])([F:24])[F:23])[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:21]=[CH:20][S: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:22]([F:24])([F:25])[F:23])[N:3]=[C:4]2[C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:15])=[O:14]

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 22998113HCID 22998113, Verbindung

Produkt 1

HCID 106192741-(4-Methanesulfonyl-phenyl)-2-thiophen-3-yl-4-trifluoromethyl-1H-imidazoleAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of the 4,5-dihydro-imidazole of step 2 (1.5 g, 3.8 mmol) and p-toluenesulfonic acid monohydrate (0.30 g, 1.5 mmol) in toluene (250 ml) was heated to reflux for 40 hours. An additional p-toluenesulfonic acid monohydrate (0.15 g, 0.78 mmol) was added. The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture (3.5 g) was chromatographed on silica gel using ethyl acetate/toluene (55/45) to give pure 3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]thiophene (0.90 g, 64%) as a white solid: mp 194°-197° C. Anal. Calc'd. for C15H11N2S2O2F3 : C, 48.38, H, 2.98, N, 7.52, S, 17.22. Found C, 48.74, H, 2.98, N, 7.56, S, 17.45.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 40 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 18 hours
  5. temperatureThe reaction mixture was cooled
  6. customthe solvent removed under reduced pressure
  7. customThe crude mixture (3.5 g) was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ab6a3aa5b14b4127be31352bc1dd8c69
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616601

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