Potassium Carbonate → 4-[1-(4-chloro-3-nitrophenacyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

HRID 553350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553350
[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]([NH2:15])=[N:12][O:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28]Br)=[CH:25][C:24]=1[N+:33]([O-:35])=[O:34]>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28][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]([NH2:15])=[N:12][O:13][N:14]=2)=[CH:25][C:24]=1[N+:33]([O-:35])=[O:34]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 7385314-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amineHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

Produkt 1

HCID 674590044-[1-(4-chloro-3-nitrophenacyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-ylamine (0.228 g, 1.14 mmol), potassium carbonate (0.40 g, 2.85 mmol) and 4-chloro-3-nitrophenacyl bromide (0.35 g, 1.25 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 solid, m.p. 198-200° C. (This compound is also listed as Example 66 in Table 1.)

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-bc19d117a55c4630b18be9f3c39e2601
Quelldatensatz
uspto-grants-2011_11
Patentnummer
USRE042890E1

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