反应详情

A solution of 3.24 g o-(cyclohexyl)-phenoxymethyloxirane (see Example 3) and 2.65 g of 1-(4-aminophenyl)-2-imidazolidinone in 60 ml isopropanol is stirred at reflux for 18 hours. The reaction mixture is filtered and the filtrate concentrated in vacuo. The residue is dissolved in 50 ml ethyl acetate and acidified to pH=1 with a solution of hydrogen chloride gas in ethyl acetate. The supernatant is decanted from the dark gum that forms and the residue is treated with ethyl acetate and 5% aqueous sodium carbonate. The ethyl acetate solution is separated, washed with 10% aqueous sodium carbonate and twice with water. After drying over anhydrous sodium sulfate the solution is treated with charcoal, filtered and concentrated in vacuo leaving a dark viscous gum. The gum is chromatographed by passing through a column of silica gel using methylene chloride/methyl alcohol as eluent to yield 1-{4-[3-(o-cyclohexylphenoxy)-2-hydroxypropylamino]-phenyl}-2-imidazolidinone, which is used directly in the next step.

1. temperatureat reflux for 18 hours
2. filtrationThe reaction mixture is filtered
3. concentrationthe filtrate concentrated in vacuo
4. dissolutionThe residue is dissolved in 50 ml ethyl acetate
5. customThe supernatant is decanted from the dark gum that
6. additionthe residue is treated with ethyl acetate and 5% aqueous sodium carbonate
7. customThe ethyl acetate solution is separated
8. washwashed with 10% aqueous sodium carbonate and twice with water
9. dry with materialAfter drying over anhydrous sodium sulfate the solution
10. additionis treated with charcoal
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customleaving a dark viscous gum
14. customThe gum is chromatographed