Chloroacetyl chloride → 5-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole

Participants

Reaction Steps

A solution of benzamidoxime (0.77 g, 5.68 mmol) and triethylamine (0.95 mL, 0.82 mmol) in toluene (10 mL) was treated with 0.45 mL (5.65 mmol) of chloroacetyl chloride at room temperature for 30 min., refluxed for 18 hours, cooled to room temperature and concentrated in vacuo. The residue was diluted with water, and extracted with ethyl acetate. The organic extracts were then washed with water and dried with MgSO4. Concentration in vacuo gave an oil which was chromatographed on silica gel using ethyl acetate, hexanes (1.9), giving 0.24 of the title compound as a light yellow oil which solidified on standing. 1H NMR (250 MHz, CDCl3) δ 8.1 (m, 2H), 7.5 (m, 3H), 4.8 (s, 2H).

Provenance & Evidence