反応 #1478581

反応方程式

1-fluoro-4-nitrobenzene

pyridine

4,7,10-trioxatridecane-1,13-diamine

→

expected product ( 19 )

収率 52.7%

N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-N-(4-nitrophenyl)amine

収率 52.7%

溶媒

water

反応条件

後処理

1. 1
   その他After reaction for 24 hours
2. 2
   温度the reaction mixture was cooled
3. 3
   抽出Next, the reaction mixture was extracted with dichloromethane
4. 4
   洗浄washed twice with water
5. 5
   乾燥dried over MgSO4
6. 6
   その他evaporated under vacuum
7. 7
   その他The crude product, isolated in the form of a yellow oil
8. 8
   その他was purified on a column of silica
9. 9
   洗浄eluting with ethyl acetate (
10. 10
    その他to separate out the dinitro derivative), and then with methanol (
11. 11
    その他to recover the expected mono-nitro derivative)

実験手順

1.41 g (0.01 mol) of 1-fluoro-4-nitrobenzene and 1.62 ml (0.02 mol) of pyridine were introduced into a three-necked flask under nitrogen. 8.75 ml (0.04 mol) of 4,7,10-trioxatridecane-1,13-diamine were added dropwise with stirring. The mixture was heated to 70° C. After reaction for 24 hours, the reaction mixture was cooled and 40 ml of distilled water were then added with vigorous stirring. Next, the reaction mixture was extracted with dichloromethane, washed twice with water, dried over MgSO4 and then evaporated under vacuum. The crude product, isolated in the form of a yellow oil comprising about 90% of expected mono-nitro derivative, was purified on a column of silica, eluting with ethyl acetate (to separate out the dinitro derivative), and then with methanol (to recover the expected mono-nitro derivative). 1.8 g of expected product (19) were obtained in the form of a dark yellow oil.

出典