反应详情

To a solution of 1.67 g of 4-{[(diphenylmethyl)amino]carbonyl}-1H-imidazole in 100 ml of dimethylformamide were added 5.03 g of potassium fluoride on alumina. With stirring, 1.35 g of α-bromooctanonitrile were added. The solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water, washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. NMR indicated a mixture of starting material with desired product, so the residue was dissolved in 200 ml of acetonitrile, and 1 g of α-bromooctanonitrile and 5 g of potassium fluoride on alumina was added. After stirring at room temperature for 2 days, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed over SiO2 and the appropriate fractions combined and concentrated in vacuo to provide 1.2 g of the desired titled intermediate, oil. MS: M+ =400

1. stirringThe solution was stirred at room temperature overnight
2. concentrationconcentrated in vacuo
3. washwashed with water
4. washwashed with a saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. additiona mixture of starting material with desired product
8. dissolutionso the residue was dissolved in 200 ml of acetonitrile
9. addition1 g of α-bromooctanonitrile and 5 g of potassium fluoride on alumina was added
10. stirringAfter stirring at room temperature for 2 days
11. filtrationthe mixture was filtered
12. concentrationthe filtrate was concentrated in vacuo
13. customThe residue was chromatographed over SiO2
14. concentrationconcentrated in vacuo