Potassium Carbonate → 6-[5-[[3-(Trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]benzothiazole

HRID 452680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452680
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3[O:14][C:13]([SH:15])=[N:12][N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][S:15][C:13]1[O:14][C:10]([C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)=[N:11][N:12]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 178527938HCID 178527938, Verbindung

Produkt 1

HCID 686640606-[5-[[3-(Trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]benzothiazoleAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 5-(benzothiazol-6-yl)-1,3,4-oxadiazole-2-thiol (235 mg, 1.00 mmol), 3-(trifluoromethyl)benzyl chloride (0.186 mL, 1.20 mmol), and potassium carbonate (207 mg, 1.50 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (321 mg, yield 82%) as colorless crystals.

Aufarbeitung

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  5. customrecrystallized from hexane/tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-6503a605ccbf430aa7b8c91a4b893aeb
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492378B2

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