Synthesis
2-Chloro-N'-hydroxyacetamidine (217 mg, 2 mmol) was mixed with ethanoic anhydride (224.4 mg, 2.2 mmol) in dichloromethane (2 mL) at room temperature and reacted for 1 hour. N,N-dimethylformamide (1 mL) was then added and the reaction mixture was heated at 130 °C for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium carbonate solution and extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product 3-(chloromethyl)-5-methyl-1,2,4-oxadiazole (59 mg, 22.2% yield) as a yellow oil, which could be used in subsequent reactions without further purification.1H NMR (CDCl3, δ ppm): 4.41 (s, 2H), 2.55 (s, 3H).
References
[1] Patent: WO2004/14902, 2004, A2. Location in patent: Page 43
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2769 - 2772
