تفاعل #613162

معادلة التفاعل

Naphthalene-1,5-diamine

1-bromooctane

potassium carbonate

→

N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine

المردود 38.3%

المذيبات

butanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with water
2. 2
   استخلاصextracted with ether three times
3. 3
   غسيلThe combined organic phase was washed three times with water
4. 4
   أخرىevaporated
5. 5
   أخرىto give black oil which
6. 6
   workup.DISTILLATIONwas distilled under reduced pressure at 90° C.
7. 7
   أخرىto yield a black tar
8. 8
   أخرىThis was purified with flash chromatography
9. 9
   أخرىto obtain colourless oil which
10. 10
    أخرىcrystallised

الإجراء التجريبي

Naphthalene-1,5-diamine (3.14 g, 19.8 mmol), 1-bromooctane (25.25 g, 0.130 mol), potassium carbonate (11.79 g, 85.3 mmol), and potassium iodide (0.05 g, 0.30 mmol) was stirred in dry butanol (150 ml) and heated to 110° C. for 36 h. The reaction was quenched with water and extracted with ether three times. The combined organic phase was washed three times with water and evaporated to give black oil which was distilled under reduced pressure at 90° C. to yield a black tar. This was purified with flash chromatography using hexane as mobile phase to obtain colourless oil which crystallised to yield N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine (2.3 g, 3.79 mmol) as white crystals. 1H-NMR (CDCl3, δ): 0.85 (t, 12H), 1.0-1.4 (m, 40H), 1.4-1.6 (m, 8H), 3.08 (t, 8H), 7.1 (d, 2H), 7.35 (t, 2H), 8.01 (d, 2H) MS MALDI-TOF (m/z): 606.574

المصدر