Furfural → 5-(Benzoxazol-2-yl)-2-(furan-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74235
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[CH:24](=O)[C:25]1[O:29][CH:28]=[CH:27][CH:26]=1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:24]([C:25]3[O:29][CH:28]=[CH:27][CH:26]=3)=[N:15][C:14]=2[CH:16]=1

Komponenten

6

Edukt 4

HCID 7362FurfuralHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Produkt 1

HCID 674982445-(Benzoxazol-2-yl)-2-(furan-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in dimethylformamide (2 mL) was added furfural (80.7 mg, 0.840 mmol) and oxone (258 mg, 0.420 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (121 mg, 49% yield) as pale yellow crystals.

Aufarbeitung

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-884566f61b1443ad8ce55796f5348a80
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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