Reaktion #62947

Reaktionsgleichung

ethyl 3-(2-mercapto-4-methyl-1,3-thiazol-5-yl)propionate

bromoacetic acid

→

ethyl 3-[2-(carboxymethylthio)-4-methyl-1,3-thiazol-5-yl]propionate

Ausbeute 152.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Sonstigethe solvent was removed in vacuo

Vorschrift

2 g (8.6 mmol) of ethyl 3-(2-mercapto-4-methyl-1,3-thiazol-5-yl)propionate were initially introduced into 40 ml of dry DMF, and 1.49 g (8.6 mmol) of bromoacetic acid were added. After 2 hours, the solvent was removed in vacuo, and 3.8 g of ethyl 3-[2-(carboxymethylthio)-4-methyl-1,3-thiazol-5-yl]propionate were obtained as an oil. The crude product was taken up in 25 ml of ethanol, 33 ml of 1N sodium hydroxide solution were added, and the reaction mixture was heated at 50° C. After the reaction was complete, the ethanol was removed in vacuo, and the aqueous residue was taken up in concentrated hydrochloric acid at pH 3.0, and the solution was extracted with ethyl acetate. 1.6 g (71%) of the title compound were obtained from the organic phase after drying with MgSO4, evaporation and crystallization with diethyl ether.

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