Reacción #1820954

Ecuación de reacción

Sodium hydroxide

1-Thia-4,7,10-triazacyclododecane-3,11-dione

diborane

HCl

→

1-Thia-4,7,10-triazacyclododecane

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solution was evaporated to dryness
2. 2
   ExtracciónThe residue was extracted with ethanol (3×50 ml)
3. 3
   Concentraciónthe extracts were concentrated
4. 4
   Otro1-thia-4,7,10-triazacyclododecane was purified by extraction (acetonitrile) and sublimation (Kugelrohr)

Procedimiento

1-Thia-4,7,10-triazacyclododecane-3,11-dione (8.10 g, 37.3 mmol) was suspended in dry THF (distilled from lithium aluminium hydride) (2000 ml) and refluxed under nitrogen for 8 hours with continuous addition of freshly generated diborane (approx. 0.4 mol in total). The reaction mixture was cooled to ambient temperature, 6N HCl (80 ml) was added, and the mixture was stirred for 1 hour. Sodium hydroxide (20 g, 0.5 mol) was added and the solution was evaporated to dryness. The residue was extracted with ethanol (3×50 ml), the extracts were concentrated and 1-thia-4,7,10-triazacyclododecane was purified by extraction (acetonitrile) and sublimation (Kugelrohr). Yield 3.73 g (53%), white solid, m.p. 51°-54° C. (uncorrected). The structure was confirmed by 1HNMR and 13CNMR.

Fuente