Triethylamine → 2-Ethylthio-5-(hex-5-ynylaminocarbonyl)thiazole

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Reaction Conditions

Reaction Steps

In this preparation 0.1 mole of 2-ethylthio-5-carboxythiazole is dissolved in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, and 0.1 moles of triethylamine is added and the resulting mixture cooled to -30° C. 0.1 Mole of ethylchloroformate is then added dropwise with stirring and the resulting mixture allowed to warm to 0° C. The mixture is then stirred for ten minutes, then cooled to -30° C and 0.11 mole of 1-aminohex-5-yne in 50 ml. of tetrahydrofuran added dropwise. The mixture is allowed to warm to room temperature (about 20° C), poured into 500 ml. of ethyl acetate, washed with water, then washed with saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The mixture is then filtered and the solvent from the resulting filtrate is evaporated under vacuum yielding 2-ethylthio-5-(hex-5-ynylaminocarbonyl)thiazole as a solid, which is then further purified by recrystallization from ethyl acetate.

Provenance & Evidence