反応 #1856081

反応方程式

1,8-diaminonaphthalene

4-chlorobutyro-phenone

→

dihydroperimidine

収率 47.4%

溶媒

toluene

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度to reflux under a nitrogen atmosphere
3. 3
   その他to remove the water
4. 4
   その他evolved from the reaction for 10 hr
5. 5
   ろ過The mixture was filtered
6. 6
   その他to remove unreacted
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo
10. 10
    その他to give 2.04 g of crude product
11. 11
    その他This was further purified by chromatography on silica gel
12. 12
    洗浄eluting with 1:1 diethyl ether/petroleum ether
13. 13
    その他collecting the initial band

実験手順

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.

出典