反应详情

Sodium hydride (0.14 g of 80% in mineral oil, 4.7 mmol) was added to a solution of 1-benzyloxy-3-(4-butylphenyl)urea (1.25 g, 4.2 mmol) in N,N-dimethylformamide (5 mL). The reaction mixture was heated briefly on a steam bath under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature then 1-bromopentane (0.63 g, 4.2 mmol) was added. The reaction mixture was heated at 90° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with water and then extracted with diethyl ether. The organic layer was washed with water, dried with magnesium sulfate and then concentrated to provide 1.47 g of crude product as a brown oil. This material was purified by flash chromatography (silica gel; 1:19 ethyl acetate:hexanes) to provide 0.96 g of 1-benzyloxy-3-(4-butylphenyl)-1-pentylurea as an oil.

1. temperatureThe reaction mixture was heated briefly on a steam bath under a nitrogen atmosphere
2. temperatureThe reaction mixture was heated at 90° C. overnight
3. temperatureThe reaction mixture was cooled to ambient temperature
4. extractionextracted with diethyl ether
5. washThe organic layer was washed with water
6. dry with materialdried with magnesium sulfate
7. concentrationconcentrated
8. customto provide 1.47 g of crude product as a brown oil
9. customThis material was purified by flash chromatography (silica gel; 1:19 ethyl acetate:hexanes)