Diiodomethane → 4-[1-(3,4-Dimethylphenoxymethyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(2-cyanoethyl)-amine

HRID 132006

Reaktionsgleichung

Reaktionsgleichung von HRID 132006
[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][C:18]#[N:19])=[N:12][O:13][N:14]=1.[C:20](=[O:23])([O-])[O-].[K+].[K+].ICI.[CH3:29][C:30]1[CH:31]=[C:32](O)[CH:33]=[CH:34][C:35]=1[CH3:36]>CN(C=O)C.C(OCC)(=O)C>[CH3:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:34][C:35]=1[CH3:36])[O:23][CH2:20][N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][C:18]#[N:19])=[N:12][O:13][N:14]=1

Komponenten

7

Edukt 4

HCID 6346DiiodomethaneHCID 72493,4-DimethylphenolHCID 11430Potassium CarbonateHCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

Produkt 1

HCID 674636294-[1-(3,4-Dimethylphenoxymethyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(2-cyanoethyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.15 g, 0.59 mmol, Example 6a), potassium carbonate (0.325 g, 2.36 mmol), diiodomethane (0.16 g, 0.59 mmol) and 3,4-dimethylphenol (0.072 g, 0.59 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. 132-135° 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-32189c7fc33341d3ba13f3040b35987d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385061B2

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