反应详情

温度

55 °C

To a solution of ethylamine in methanol (2.0 M, 150 mL, 300 mmol) was added 1-fluoro-2-nitrobenzene (8 mL, 75.7 mmol). The reaction mixture was placed in a sealed vessel and heated to 55° C. for 15 hours. The solvent was removed in vacuo and residue taken up in ethyl acetate (200 mL), washed with a saturated aqueous sodium bicarbonate solution (80 mL), and dried over anhydrous sodium sulfate (50 g). After removal of solvent, the residue was dissolved in anhydrous THF (150 mL) and to the solution added sodium borohydride (5.8 g, 153 mmol) and 5% palladium on carbon (150 mg). Methanol (25 mL) was then added at room temperature under nitrogen in a dropwise manner. After addition, the reaction mixture was stirred at room temperature for about 30 minutes until the reaction was complete and filtered through a pad of celite. The filtrate was taken up in ethyl acetate (200 mL), washed with a saturated aqueous ammonium chloride solution (80 mL), dried (Na2SO4), and concentrated. The residue was dissolved in anhydrous THF (200 mL) and to the solution was added 1,1′-carbonyldiimidazole (10 g, 62 mmol). The mixture was stirred at room temperature under nitrogen for 12 hours and ethyl acetate (250 mL) and a cold 3N aqueous HCl solution (200 mL) added. The organic layer was separated, dried (Na2SO4), and concentrated to afford 1-ethyl-1,3-dihydro-benzimidazol-2-one as a white solid (8.5g, 69% for three steps). MS (ES) m/z 163.2.

1. customThe reaction mixture was placed in a sealed vessel
2. customThe solvent was removed in vacuo and residue
3. washwashed with a saturated aqueous sodium bicarbonate solution (80 mL)
4. dry with materialdried over anhydrous sodium sulfate (50 g)
5. customAfter removal of solvent
6. dissolutionthe residue was dissolved in anhydrous THF (150 mL) and to the solution
7. additionAfter addition
8. filtrationfiltered through a pad of celite
9. washwashed with a saturated aqueous ammonium chloride solution (80 mL)
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated
12. dissolutionThe residue was dissolved in anhydrous THF (200 mL) and to the solution
13. stirringThe mixture was stirred at room temperature under nitrogen for 12 hours
14. customThe organic layer was separated
15. dry with materialdried (Na2SO4)
16. concentrationconcentrated