반응 #1984561

반응 방정식

Naphthalene-1,5-diamine

1-bromooctane

potassium carbonate

→

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

수율 38.3%

용매

butanol

반응 조건

후처리

1. 1
   기타The reaction was quenched with water
2. 2
   추출extracted with ether three times
3. 3
   세척The combined organic phase was washed three times with water
4. 4
   기타evaporated
5. 5
   기타to give black oil which
6. 6
   workup.DISTILLATIONwas distilled under reduced pressure at 90° C.
7. 7
   기타to yield a black tar
8. 8
   기타This was purified with flash chromatography
9. 9
   기타to obtain colourless oil which
10. 10
    기타crystallised

실험 절차

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

출처