Potassium Carbonate → 4-[1-(4-Chlorophenacyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(3-hydroxypropyl)-amine

HRID 132007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132007
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[N:12][O:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:36]=[CH:35][C:30]([C:31](=[O:34])[CH2:32]Br)=[CH:29][CH:28]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:26][C:27]1[CH:36]=[CH:35][C:30]([C:31](=[O:34])[CH2:32][N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=[C:2]2[C:10]2[C:11]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[N:12][O:13][N:14]=2)=[CH:29][CH:28]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 1364137544-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

Produkt 1

HCID 674619604-[1-(4-Chlorophenacyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(3-hydroxypropyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine (0.70 g, 0.27 mmol), potassium carbonate (0.472 g, 3.42 mmol) and 4-chlorophenacyl bromide (0.069 g, 0.29 mmol) in DMF (5 ml) is stirred at room temperature for 16 hours. The reaction mixture is diluted with ethyl acetate, washed with water and dried over sodium sulphate. Filtration of the sodium sulphate, concentration of the filtrate under reduced pressure and chromatography of the residue on silicagel using hexane-ethyl acetate as eluent gives the title compound as a yellowish solid, m.p. 166-169° C.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over sodium sulphate
  3. filtrationFiltration of the sodium sulphate, concentration of the filtrate under reduced pressure and chromatography of the residue on silicagel

Quellen und Nachweise

ORD-Eintrag
ord-d3dde619be434593a6dd14a86323831a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385061B2

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