Synthesis and study of some 4-chlorophenoxy methyl substituted amido1, 3, 4-oxadiazoles, 1, 3, 4- thiadiazoles and 1, 2, 4-triazoles from 4-chloro phenoxy acetic acid

Abstract EN

In this paper the synthesis of some substituted 1,3,4-oxadiazole, 1,3,4-thiadiazoles and 1,2,4-triazoles is reported.

4-Chlorophenol was treated with chloroacetic acid to give 4-chlorophenoxy acetic acid (C1) which was reacted with thionyl chloride followed by methyl alaninate (C3) to give the methyl ester (C4).

The ester (C4) was converted to corresponding hydrazide (C5) by it's reaction with hydrazine hydrate in ethanol.

Hydrazide (C5) was treated with carbon disulfide in alcoholic potassium hydroxide to give substituted 1,3,4-oxadiazole (C6), while the reaction of hydrazide (C5) with ally isothiocyanate and with phenyl isothiocyanate gave substituted thiosemicarbazides (C7) and (C13) respectively.

Thiosemicarbazides (C7 and C13) were converted to substituted 1,3,4-thiadiazoles (C8 and C14) and 1,2,4-triazoles (C9 and C15) by their reactions with concentrated sulfuric acid and with aqueous sodium hydroxide solution respectively.

The reaction of acid hydrazide (C5) with ammonium thiocyanate gave thiosemicarbazide (C10) from which substituted 1,3,4-thiadiazole (C11) and 1,2,4-triazole (C12) were synthesized by it's reaction with concentrated sulfuric acid and with aqueous sodium hydroxide solution respectively.

The structures of the synthesized compounds were established on the bases of U.V and I.R spectrum analysis and physical measures.