Reaktion #68768

Reaktionsgleichung

water

TEMPOL

chlorambucil

DCC

DCC

chlorambucil

TEMPOL

→

Chlorambucil TEMPOL

Ausbeute 87.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solid materials formed
2. 2
   Filtrationwere filtered off
3. 3
   Waschenthe filtrate was washed with 1 M HCl (1 ml)
4. 4
   TrocknenThe organic phase was dried over MgSO4
5. 5
   Sonstigeevaporated in vacuum
6. 6
   Sonstigeto give 0.4 g of CT corresponding to a yield of 87%

Vorschrift

DCC coupling reaction was used to couple the carboxylic group of chlorambucil with the hydroxyl group of TEMPOL with the loss of a water molecule. To a stirred solution of TEMPOL (0.172 g, 1 mmol) and chlorambucil (0.304 g, 1 mmol) in methylene chloride (5 ml) at 0° C. under argon, DCC (0.206 g, 1 mmol) (Dicyclohexyl carbodiimide) and DMAP (0.0307 g, 0.25 mmol) (Dimethyl amino pyridine) were added and the reaction mixture was stirred for 12 hrs at room temperature. The solid materials formed were filtered off, and the filtrate was washed with 1 M HCl (1 ml) followed by saturated NaHCO3 (2 ml) and brine (2 ml). The organic phase was dried over MgSO4 and evaporated in vacuum to give 0.4 g of CT corresponding to a yield of 87%. TLC (Thin Layer Chromatography) of the product showed a single spot only.

Quelle