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5-BENZYL-[1,3,4]OXADIAZOLE-2-THIOL synthesis

5synthesis methods
-

Yield:23288-90-6 93%

Reaction Conditions:

with sodium hydroxide in ethanol; for 4 h;Reflux;

Steps:



General procedure: Method A: With reference to Manjunatha et a/., the 1 ,3,4-oxadiazole derivatives were synthesized as described below:[6] The appropriate hydrazide (10.0 mmol) was dissolved in ethanol 96% (30 mL) with addition of sodium hydroxide (0.400 g, 10.0 mmol). After the addition of carbon disulfide 0.776 g, 10.2 mmol) the reaction batch was refluxed for four hours. The mixture was cooled to room temperature. Addition of 1 M hydrochloric acid (10.0 mL) led to precipitation. The precipitates were filtered, washed with water and recrystallized from ethanol. 5-Benzyl-1 ,3,4-oxadiazole- -thiol:[10] The compound was synthesized as described in method A; light yellow powder (Yield: 93%). Mp = 125 - 127 °C. (129 - 130 °Ct10]) 1H-NMR (DMSO-de, 400 MHz): 4.14 (s, 2H, CH2), 7.28-7.41 (m, 5H, ArH), 14.12 (s, br, 1 H, SH). 13C-NMR (DMSO-d6, 100 MHz): 31.0 (sec. C); 127.4, 128.8 (2C), 129.0 (2 C) (tert. C); 133.5, 163.0, 177.8 (quat. C). MS (El): m/z (%) = 192 [Mf (69).

References:

WO2014/79545,2014,A1 Location in patent:Page/Page column 36; 37; 38