Ethanol → HCID 9975470, compound

Temperature

100 °C

This compound was synthesized following the procedure of European Patent 0 287 465 A1, Oct. 19, 1988. A mixture of 2-methyl-1,4,7,10,13-penta(p-toluenesulfonyl)-1,4,7,10,13-pentaazacyclopentadecane prepared as in Example 2D (20.6 g, 0.0206 mole) and concentrated H2SO4 (75 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 70 h. To the resulting brown solution ethanol (100 ml) was added dropwise with stirring at 0° C., followed by ethyl ether (1l). The off-white oily solid was filtered and washed thoroughly with ethyl ether. The solid was then dissolved in H2O (100 ml) and the resulting solution was washed with ethyl ether. The pH of the solution was adjusted to 10-11 with 10N NaOH and the solvent was removed in vacuo. Ethanol (2×500 ml) was then added and removed in vacuo. The resulting brown oily solid was extracted with hot THF (2×500 ml) and filtered. The filtrates were combined and the solvent was removed in vacuo. The residue was dissolved in THF (100 ml) and filtered to remove insoluble impurities. The solvent was removed in vacuo to give the crude product as a yellow crystalline solid which was then dissolved in CH3CN and filtered to remove impurities. Crystallization occurred upon cooling the filtrate to -20° C. Recrystallization from cold (-20° C.) CH3CN gave 1.30 g (28% yield) of the product as an off-white crystalline solid: mp 73°-5°C; 1H NMR (CDCl3) δ1.02 (d, J=6.2 Hz, 3 H), 1.71 (br s, 5 H), 2.36 (m, 1 H), 2.72 (m, 18 H); Anal. calcd. for C11H27N5 : C, 57.60; H, 11.87; N, 30.53: Found: C, 57.68; H, 11.34; N, 30.48.

1. customThis compound was synthesized
2. stirringwith stirring at 0° C.
3. filtrationThe off-white oily solid was filtered
4. washwashed thoroughly with ethyl ether
5. dissolutionThe solid was then dissolved in H2O (100 ml)
6. washthe resulting solution was washed with ethyl ether
7. customthe solvent was removed in vacuo
8. additionEthanol (2×500 ml) was then added
9. customremoved in vacuo
10. extractionThe resulting brown oily solid was extracted with hot THF (2×500 ml)
11. filtrationfiltered
12. customthe solvent was removed in vacuo
13. dissolutionThe residue was dissolved in THF (100 ml)
14. filtrationfiltered
15. customto remove insoluble impurities
16. customThe solvent was removed in vacuo
17. customto give the crude product as a yellow crystalline solid which
18. filtrationfiltered
19. customto remove impurities
20. customCrystallization
21. temperatureupon cooling the filtrate to -20° C
22. customRecrystallization from cold (-20° C.) CH3CN

ORD record

ord-b6109018d46947be8a41c6d9a3a55820

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05610293