Reaktion #831257

Reaktionsgleichung

4-(2-chloroethyl)-1H-imidazole hydrochloride

sodium hydride

2-naphthol

→

4-[2-(2-Naphthyloxy)ethyl]-1H-imidazole

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is heated at 100° C. for 3 days
2. 2
   Sonstigethe solvent is evaporated under reduced pressure
3. 3
   ExtraktionThe excess 2-naphthol is extracted with diethyl ether under acidic conditions (dilute hydrochloric acid)
4. 4
   Extraktionthe product is extracted with diethyl ether
5. 5
   EinengenThe ethereal extracts are concentrated
6. 6
   Sonstigethe residue obtained
7. 7
   Sonstigeis crystallized from a methanol/water (1/2) mixture, M.p.: 157°-158° C.

Vorschrift

240 mg (60% in oil, 6 mmol) of sodium hydride are added to a solution of 1.73 g (12 mmol) of 2-naphthol in 10 ml of dimethylformamide. The mixture is stirred at room temperature for 3 hours under nitrogen. 200 mg (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalytic amount) are added and the mixture is heated at 100° C. for 3 days and then the solvent is evaporated under reduced pressure. The excess 2-naphthol is extracted with diethyl ether under acidic conditions (dilute hydrochloric acid). The aqueous solution is basified with potassium carbonate and the product is extracted with diethyl ether. The ethereal extracts are concentrated and the residue obtained is crystallized from a methanol/water (1/2) mixture, M.p.: 157°-158° C.

Quelle