Reaktion #499523

Reaktionsgleichung

5-[4-[6-(3-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

n-hexyl isocyanate

triethylamine

→

title compound

Ausbeute 67.8%

1-(3-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-3-n-hexylurea

Ausbeute 67.8%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto stand overnight
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   Sonstigepartitioned between ethyl acetate and water
4. 4
   WaschenThe extract was washed with saturated aqueous sodium chloride solution
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was chromatographed on a silica gel column
8. 8
   SonstigeThe product was recrystallized from ethyl acetate

Vorschrift

A mixture of 5-[4-[6-(3-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), n-hexyl isocyanate (280 mg), triethylamine (153 mg) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 7 hours and then allowed to stand overnight. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane=3:1→4:1→ethyl acetate→ethyl acetate:methanol=15:1 as the eluant. The product was recrystallized from ethyl acetate to afford the title compound (298 mg, mp 143.7-146.9° C.).

Quelle