反应详情

温度

100 °C

To 3-bromobenzoic acid (1.2 g, 5.7 mmol) in toluene (20 mL) was added triethylamine (0.91 mL, 6.5 mmol) and diphenoxyphosphoryl azide (1.3 mL, 6.2 mmol) and the mixture was heated to 100° C. while stirring. After 1 hour 4-[(4-cyclohex-1-enylphenylamino)methyl]benzoic acid methyl ester (prepared similarly as described in example 1, step 1) (1.6 g, 5 mmol) was added and heating was continued for additional 1.5 hour. After cooling to room temperature the mixture was transferred with ethyl acetate (50 mL) to a separatory funnel. The organic mixture was washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), backwash with ethyl acetate (50 mL). The organic phases were collected, dried (sodium sulphate) and the solvent removed in vacuo to yield a brown oil that was purified on silica column eluted with DCM to afford 700 mg of 4-[3-(3-bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoic acid methyl ester.

1. additionwas added
2. temperatureheating
3. temperatureAfter cooling to room temperature the mixture
4. washThe organic mixture was washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), backwash with ethyl acetate (50 mL)
5. customThe organic phases were collected
6. dry with materialdried (sodium sulphate)
7. customthe solvent removed in vacuo
8. customto yield a brown oil that
9. customwas purified on silica column
10. washeluted with DCM