3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide synthesis

Yield:883028-82-8 92%

Reaction Conditions:

with hydrazine in ethanol;water at 20; for 16 h;

Steps:

Step 2: synthesis of 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole -5-carbohydrazide

To a solution of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (80.0 g, 265 mmol) in EtOH (800 ml) was added NH2NH2.H2O (85%, 76.0 ml, 1,325 mmol). The reaction mixture was stirred at RT for 16 h.The desired compound precipitated from the reaction mixture and was filteredand washed with EtOH (200 ml) to produce 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide (70.2 g, 92%) as a light yellow solid, which was used for the next step without further purification. 1H NMR (600 MHz, Methanol-d4): δ8.24 (d, J = 8.8 Hz, 2 H), 7.47 (d, J = 8.6 Hz, 2 H). 13C NMR (126 MHz, DMSO-d6):δ 166.9, 129.4, 124.7, 121.7, 119.9 (q, J = 258 Hz). 19F NMR (471 MHz, DMSO-d6):δ -56.6. HRMS (ESI+) m/z: [M + H]+ calculated for C10H8F3N4O3, 289.0543; found,289.0538.

References:

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