反応 #499523

反応方程式

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

n-hexyl isocyanate

triethylamine

→

title compound

収率 67.8%

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

収率 67.8%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.WAITto stand overnight
2. 2
   濃縮The reaction mixture was concentrated
3. 3
   その他partitioned between ethyl acetate and water
4. 4
   洗浄The extract was washed with saturated aqueous sodium chloride solution
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   濃縮concentrated
7. 7
   その他The residue was chromatographed on a silica gel column
8. 8
   その他The product was recrystallized from ethyl acetate

実験手順

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.).

出典