Carbon Disulfide → 5-(4-Methoxybenzyl)-1,3,4-oxadiazole-2-thiol

Participants

Reaction Steps

A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid).

Provenance & Evidence