Ethanol → 1,4,7,10,13-Pentaazacyclohexadecane

Temperatur

100 °C

A mixture of 1,4,7,10,13-penta(p-toluenesulfonyl)-1,4,7,10,13-pentaazacyclohexadecane prepared as in Example 1D (30 g, 0.030 mole) and concentrated H2SO4 (100 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 69 h. To the resulting brown solution, ethanol (200 mL) was added dropwise with stirring at 5° C., followed by ethyl ether (500 ml). The tan solid was filtered and washed thoroughly with ethyl ether. The solid was then dissolved in H2O (75 ml), the pH was adjusted to 10 with 10N NaOH, and the solution was extracted with CHCl3 (6×200 ml). The extracts were combined and dried (Na2SO4), and the solvent was removed in vacuo. The resulting yellow solid was purified by recrystallization from hexane to give 1.0 g (15% yield) of the product as colorless needles: mp 109-110.5° C.; 1H NMR (CDCl3)δ 1.72 (quint, J=5.4 Hz, 2 H), 1.76 (br s, 5 H), 2.73 (m, 20 H); Anal. calcd. for C11H27N5: C, 57.60; H, 11.86; N, 30.53. Found: C, 57.77; H, 12.35; N, 30.57.

1. stirringwith stirring at 5° C.
2. filtrationThe tan solid was filtered
3. washwashed thoroughly with ethyl ether
4. dissolutionThe solid was then dissolved in H2O (75 ml)
5. extractionthe solution was extracted with CHCl3 (6×200 ml)
6. dry with materialdried (Na2SO4)
7. customthe solvent was removed in vacuo
8. customThe resulting yellow solid was purified by recrystallization from hexane

ORD-Eintrag

ord-05e0efe5d1964e3b9ed9758d8d2c7eb3

Quelldatensatz

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06204259B1