Ethanol → HCID 10384442, compound

Participants

Reaction Conditions

Reaction Steps

A mixture-of 1,4,7,11,14-penta(p-toluenesulfonyl)-1,4,7,11,14-pentaazacyclopentadecane prepared as in Example 11C (26.3 g, 0.0258 mole) and concentrated H2SO4 (80 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 72 h. To the resulting brown solution, ethanol (160 mL) was added dropwise with stirring at 0° C. followed by ethyl ether (400 ml). The resulting tan solid was filtered and dried in vacuo over P2O5. The tarry solid was then dissolved by the addition of 10N NaOH and the salts were removed by filtration. The solution was then extracted with CHCl3 (6×200 ml). The extracts were combined, dried (Na2SO4) and the solvent was removed in vacuo to give an oil which crystallized on standing. The crude product was dissolved in hexane and insoluble impurities were removed by filtration. Upon cooling to -20° C., 2.28 g (36% yield) of the product was obtained as colorless needles: mp 49°-51° C.; 1H NMR (CDCl3) δ1.69 (m, 4 H), 1.78 (br s, 5 H), 2.76 (m, 20 H). Exact mass: (M+H)+: calcd., 244. 2501; Found: 244.2557 (C12H30N5).

Provenance & Evidence