Potassium Carbonate → 2-(2,3-Dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)thio]methyl]-1,3,4-oxadiazole

HRID 452703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452703
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH2:14][CH2:13][C:12]=3[CH:16]=2)=[N:6][N:7]=1.[F:17][C:18]1[CH:19]=[C:20]([SH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[O:15]1[C:11]2[CH:10]=[CH:9][C:8]([C:5]3[O:4][C:3]([CH2:2][S:24][C:20]4[CH:21]=[CH:22][CH:23]=[C:18]([F:17])[CH:19]=4)=[N:7][N:6]=3)=[CH:16][C:12]=2[CH2:13][CH2:14]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 75710m-FluorobenzenethiolHCID 621997482-(Chloromethyl)-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole

Produkt 1

HCID 445904152-(2,3-Dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)thio]methyl]-1,3,4-oxadiazoleAusbeute 14,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-(chloromethyl)-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole (0.16 g, 0.68 mmol), 3-fluorothiophenol (57 μL, 0.68 mmol) and potassium carbonate (0.10 g, 0.75 mmol) in N,N-dimethylformamide (5 mL) was stirred overnight at room temperature. 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 silica gel column chromatography (hexane/ethyl acetate=2/1) and recrystallized from hexane/ethyl acetate to give the title compound (32 mg, yield 14%) 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 silica gel column chromatography (hexane/ethyl acetate=2/1)
  5. customrecrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-766414b31d4840a69998bd9b7fac7c65
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492378B2

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