反应详情

To a solution of 5-chloro-2-methylbenzohydrazide (2.70 g, 14.62 mmol) prepared as in Example 1, Step B, in toluene (100 mL) was added 4-azido-1-phenylbutan-1-one (3.04 g, 16.1 mmol) prepared as in Example 70, Step A, followed by p-toluenesulfonic acid monohydrate (0.28 g, 1.46 mmol). The reaction was heated to reflux and stirred under a Dean-Stark trap for 16 hours. The cooled mixture was diluted with EtOAc (300 mL) and washed with NaHCO3 (100 mL). The aqueous layer was extracted with EtOAc (100 mL) and the combined organics were washed with brine (100 mL), dried over Na2SO4 and concentrated. The residue was triturated with ether and filtered to afford the product (3.09 g, 59%) as a tan solid.

1. temperatureThe reaction was heated
2. temperatureto reflux
3. washwashed with NaHCO3 (100 mL)
4. extractionThe aqueous layer was extracted with EtOAc (100 mL)
5. washthe combined organics were washed with brine (100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe residue was triturated with ether
9. filtrationfiltered