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Abstract
The reaction of thiocarbohydrazide (1) with benzilic acid (2) at the melting temperature (160-170 °C) allows an improved preparation of 3-(α,α-diphenyl-α-hydroxymethyl)-4-amino-1,2,4-triazoline-5-thione (3). The compound (3) reacts easily with suitable carboxylic acids in presence of phosphorous oxychloride to afford 1,2,4-triazolo [3,4-b] [1,3,4] thiadiazole ring systems (4a-g). The synthesized products were confirmed by physical and spectral methods.
Highlights
The reaction of thiocarbohydrazide (1) with benzilic acid (2) at the melting temperature (160-170 °C) allows an improved preparation of 3-(α,α-diphenyl-αhydroxymethyl)-4-amino-1,2,4-triazoline-5-thione (3)
Infrared spectra (v cm-1) were recorded on a Pye Unicam SP200 Perkin-Elmer spectrophotometer using KBr disk. 1H-NMR spectra were determined on Hitachi Perkin-Elmer spectrophotometer (60MHz) using TMS as internal reference
A mixture of thiocarbohydrazide (1) (1.06 gm, 0.01 mole) and benzilic acid (2) (2.28 gm, 0.01 mole)was heated carefully to 160-170 oC until melting occurred, it was heated at 60 oC for 15 minutes in water-bath
Summary
The reaction of thiocarbohydrazide (1) with benzilic acid (2) at the melting temperature (160-170 °C) allows an improved preparation of 3-(α,α-diphenyl-αhydroxymethyl)-4-amino-1,2,4-triazoline-5-thione (3). أمينو-4-( )الفا – ألفا – ثنائي فينيل – الفا – هيدروكسي مثيل-3 طريقة محسنة لتحضير Alkyl and aryl substituted derivatives of fused heterocyclic system were obtained first (Kanaoka, 1957) both through dehydrative ring closure of 4-acylamino-5-triazole-5-thiols or by the reaction of 1,3,4-thiadiazole-2-yl hydrazine with ortho esters. The similar compounds were prepared by ring closure of 5-substituted-4-amino-3-mercapto(4H)-1,2,4-triazoles using acyl chlorides in the presence of phosphoryl chloride (Potts and Huseby, 1966).
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