Potassium Carbonate → 5,6-Dichloro-2-(2-trifluoromethyl-oxazolidin-2-yl)-1H-benzimidazole

HRID 2405076

Reaktionsgleichung

Reaktionsgleichung von HRID 2405076
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Br.Br[CH2:20][CH2:21][NH2:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3([C:10]([F:13])([F:11])[F:12])[NH:22][CH2:21][CH2:20][O:14]3)=[N:6][C:5]=2[CH:15]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27742172-Bromoethylamine hydrobromideHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Produkt 1

HCID 583331665,6-Dichloro-2-(2-trifluoromethyl-oxazolidin-2-yl)-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(5,6-DiChloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (594 mg), 2-bromoethylamine-hydrobromide (860 mg) and potassium carbonate (871 mg) were dissolved in DMF (5 mL). The reaction mixture was stirred for 18 hrs at ambient temperature, then diluted with ethyl acetate (50 mL), washed with water (50 mL) and brine (2×20 mL). The extracts were dried over Na2SO4, filtered, concentrated, and purified by column chromatography (SiO2; 40% ethyl acetate/hexanes) to yield the title compound as a yellow solid.

Aufarbeitung

  1. washwashed with water (50 mL) and brine (2×20 mL)
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (SiO2; 40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-86c6e423292b4705a63aa15eb1983f58
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802865B2

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