N-Hydroxyacetamidine → 5-(3-Methoxymethoxy-4-methyl-phenyl)-3-methyl-[1,2,4]oxadiazole

Beteiligte Stoffe

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Reaktionsschritte

A mixture of 3-methoxymethoxy-4-methyl-benzoic acid (1.96 g, 10 mmol), 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide (1.92 g, 10 mmol, Aldrich), and 1-hydroxybenzotriazole hydrate (1.5 g, 10 mmol, Aldrich) was stirred at room temperature for 30 minutes. Acetamide oxime (0.74 g, 10 mmol) (GFS Chemicals) was added and the mixture heated at 140° C. with magnetic stirring for 2 hours. After cooling, the mixture was partitioned between ethyl acetate (2×100 mL) and saturated aqueous sodium bicarbonate solution (100 mL). Ethyl acetate solutions were combined and concentrated to give crude 5-(3-methoxymethoxy-4-methyl-phenyl)-3-methyl-[1,2,4]oxadiazole. (Yield 1.23 g, 52.5%).

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