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

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Reaction Steps

Chloroacetylchloride (2.64 ml, 3.74 g, 3.3×10-2 mol) in benzene (10 ml) was added dropwise to a stirred solution of 2-(2-dimethylaminophenylthio)acetamidoxime (6.75 g, 0.03 mol) and triethylamine (4.17 ml) in benzene (20 ml). The mixture was stirred at ambient temperature for 10 hours then refluxed for 1 hour. The cooled mixture was taken up in ether and 5% aqueous sodium bicarbonate solution. The organic layer was washed with water and saturated aqueous sodium chloride solution dried and evaporated to dryness to give a brown oil. Chromatography on silica gel (135 g), eluting with hexane:ether (3:1) gave 5-(chloromethyl)-3-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole as a colourless oil, nmr δ(CDCl3) 2.78(6H, CH3), 4.20(2H, ,--CH2 --), 4.65 (2H, ,--CH2 --), 6.8-7.4 (4H, m, aromatic hydrogens).

Provenance & Evidence