Reaktion #417185

Reaktionsgleichung

sodium chloride

sodium hydride

methyl 4-mercaptobenzoate

1-(2-chloro-2-phenylethyl)imidazole

→

title compound

Ausbeute 30.4%

Methyl 4-[1-phenyl-2-(imidazol-1-yl)ethylthio]benzoate

Ausbeute 30.4%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.ADDITIONwas added to the thus obtained solution
3. 3
   Temperaturthe mixture was then heated at 65° to 70° C. for 6 hours
4. 4
   Extraktionthe resulting solution was extracted with diethyl ether
5. 5
   WaschenThe extract was washed with water
6. 6
   Trocknendried over anhydrous potassium carbonate
7. 7
   Sonstigethe solvent was removed by distillation
8. 8
   SonstigeThe residue was purified by column chromatography through silica gel (eluent: ethyl acetate:triethylamine=40:1 by volume)

Vorschrift

1.5 g of methyl 4-mercaptobenzoate was dissolved in 8 ml of dry dimethylformamide, and the resulting solution was added to 388 mg of a 55% w/w suspension of sodium hydride in mineral oil, whilst ice-cooling, and then the mixture was stirred at room temperature for 30 minutes. A solution of 1.5 g of 1-(2-chloro-2-phenylethyl)imidazole dissolved in 8 ml of dry dimethylformamide was added to the thus obtained solution, and the mixture was then heated at 65° to 70° C. for 6 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium chloride, and the resulting solution was extracted with diethyl ether. The extract was washed with water and dried over anhydrous potassium carbonate, and then the solvent was removed by distillation. The residue was purified by column chromatography through silica gel (eluent: ethyl acetate:triethylamine=40:1 by volume) to obtain 747 mg of the title compound as a colorless powder.

Quelle