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ChemicalBook CAS DataBase List 4-(1H-1,2,4-TRIAZOL-1-YL)BENZALDEHYDE
27996-86-7

4-(1H-1,2,4-TRIAZOL-1-YL)BENZALDEHYDE synthesis

6synthesis methods
1,2,4-Triazole

288-88-0

4-Fluorobenzaldehyde

459-57-4

4-(1H-1,2,4-TRIAZOL-1-YL)BENZALDEHYDE

27996-86-7

GENERAL METHOD: A mixture of 4-fluorobenzaldehyde (10 mmol) and 1,2,4-triazole (10 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 20 mL). Potassium carbonate (K2CO3, 12 mmol) was added to the above stirred solution in portions over 15 minutes. The reaction mixture was stirred at 110°C for 10-12 hours. After completion of the reaction, the heating was stopped and the potassium carbonate was removed by filtration. The filtrate was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, washed with water (3 x 15 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (60-120 mesh) with the eluent of methanol:chloroform (1:99, v/v) to obtain the target compound 4-(1-1,2,4-triazolyl)benzaldehyde.

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Yield:-

Steps:

Multi-step reaction with 3 steps
1: 48 percent / NaH / dimethylsulfoxide / 18 h / 100 °C
2: 77 percent / NaBH4, CaCl2 / tetrahydrofuran / Ambient temperature
3: 49 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 1.5 h / Ambient temperature

References:

Artico;Silvestri;Stefancich;Avigliano;Di Giulio;Maccarrone;Agostinelli;Mondovi;Morpurgo [European Journal of Medicinal Chemistry,1992,vol. 27,# 3,p. 219 - 228]

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