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3-(CHLOROMETHYL)-5-(4-CHLOROPHENYL)-1,2,4-OXADIAZOLE synthesis

4synthesis methods
-

Yield:-

Reaction Conditions:

with sodium hydrogencarbonate in hexane;water;ethyl acetate;acetone;toluene;

Steps:

10 3-Chloromethyl-5-(4-chlorophenyl)-1,2,4-oxadiazole

PREPARATION 10 3-Chloromethyl-5-(4-chlorophenyl)-1,2,4-oxadiazole A solution of 2-chloroacetamidoxime (0.5 g) and sodium bicarbonate (0.78 g) in 10 mL of anhydrous acetone was treated with 4-chlorobenzoyl chloride (0.58 mL) at room temperature for 2 hours, concentrated in vacuo, dissolved in water and extracted with ethyl acetate. The organic layers were combined, dried with MgSO4 and concentrated to a semi-solid. This material was redissolved in toluene (50 mL). refluxed under nitrogen for 15 hours, cooled and absorbed on to silica gel. Chromatography using ethyl acetate:hexane (1:9) gave the pure title product as a light yellow solid, mp 79-80° C. Mass spectrum m/e: 228 (M+), 1 H NMR (250 MHz, CDCl3) δ 8.1 (d, 2H), 7.5 (d, 2H), 4.7 (s, 2H).

References:

US6166020,2000,A