反应详情

1,9-Bis[4-(hydroxyaminomethyl)phenoxy]nonane (1.07 g) was dissolved in 75 ml of tetrahydrofuran-dimethylformamide (4:1) and, in an atmosphere of argon and with ice-cooling, 0.75 ml of ethoxycarbonyl isocyanate was added dropwise to the solution. After 10 minutes of stirring, 1N sodium hydroxide aqueous solution was added dropwise to the reaction mixture with water-cooling, followed by 2 hours of stirring at room temperature. The solvent was evaporated under a reduced pressure, and the thus obtained residue was mixed with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride aqueous solution in that order and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under a reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the thus obtained 0.78 g of crude product obtained from fractions of chloroform-methanol (40:1) elution was recrystallized from methanol to obtain 0.69 g of 1,9-bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]nonane.

1. temperaturecooling
2. temperaturecooling
3. waitfollowed by 2 hours
4. stirringof stirring at room temperature
5. customThe solvent was evaporated under a reduced pressure
6. additionthe thus obtained residue was mixed with 1N hydrochloric acid
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with water and saturated sodium chloride aqueous solution in that order
9. dry with materialdried over anhydrous magnesium sulfate
10. customThen, the solvent was evaporated under a reduced pressure
11. customthe thus obtained 0.78 g of crude product obtained from fractions of chloroform-methanol (40:1) elution
12. customwas recrystallized from methanol