反应详情

A stirred mixture of 1.411 g of 1,8-diaminonaphthalene, 1.629 g of 4-chlorobutyro-phenone, 3 mg of p-toluenesulfonic acid monohydrate, and 10 mL of toluene was heated to reflux under a nitrogen atmosphere using a Dean-Stark trap to remove the water evolved from the reaction for 10 hr. The mixture was filtered to remove unreacted starting material, partioned between ethyl acetate and 5% sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 2.04 g of crude product. This was further purified by chromatography on silica gel, eluting with 1:1 diethyl ether/petroleum ether, and collecting the initial band to yield 0.719 g of dihydroperimidine intermediate.

1. temperaturewas heated
2. temperatureto reflux under a nitrogen atmosphere
3. customto remove the water
4. customevolved from the reaction for 10 hr
5. filtrationThe mixture was filtered
6. customto remove unreacted
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give 2.04 g of crude product
11. customThis was further purified by chromatography on silica gel
12. washeluting with 1:1 diethyl ether/petroleum ether
13. customcollecting the initial band