| 89.62% |
In ethanol; acetic acid; for 0.897222h;Microwave irradiation; |
General procedure: 4-Amino-1,2,4-triazole (0.005 mol) was taken in 150 mL beaker and dissolved in ethanol (10 mL). Equimolar amount of substituted benzaldehyde was added to the ethanolic solution. Then, 0.5 mL of glacial acetic acid was added dropwise to the reaction mixture and stirred with glass rod. The contents were irradiated in MW at 360W for required time with continuous monitoring by TLC. Then the reaction mixture was filtered. Crude product was recrystallized from ethanol to obtain pure compound. Same procedure was repeated but with different amount of catalysts, i.e., 0.75 mL and 1 mL. The progress of reaction was monitored by TLC after 10 s interval. On completion of reaction, resultant mass was filtered and recrystallized from ethanol. The same procedure was used for the synthesis of rest of the compounds. The work was continued by using different amounts of lemon juice as catalyst at 360 W for required time. 4-((4H-1,2,4-triazol-4-ylimino)methyl)phenol (I) IR (numax, KBr, cm-1): 3378 (O-H str.), 3107 (aromatic -C-H str.), 1665 (C=N str.), 1590 (N-N str.), 1607, 1567, 1507, 1475 (C=C str.), 1311 (O-H bending), 1275 (C-N str.), 1168 (C-O), 861 (C-N bending), 755 (C-H bending), and 771/cm (C=C bending); 1H NMR (DMSO-d6, 400 MHz, delta): delta 10.23 (s, 1H, OH), 8.98 (s, 2H, -CH=), 8.91 (s, IH, -CH=N-), 7.71-6.89 (m, 4H, Ar-H); 13C NMR (DMSO-d6, 100 MHz, delta): delta 159.3, 157.4, 148, 131.67, 126.13, 116.89; Analysis calculated for C9H8N4: C, 57.44; H, 4.25; N, 29.78. Found: C, 57.45; H, 4.26; N, 29.79. |
| 76% |
With sulfuric acid; In ethanol;Reflux; |
General procedure: In a typical procedure, 3-arylimino-1,2,4-triazoles and 4-arylimino-1,2,4-triazoles 1-25 were synthesized by mixing 3-amino-1,2,4-triazole or <strong>[584-13-4]4-amino-1,2,4-triazole</strong> (2 mmol), substituted benzaldehydes (2 mmol) and H2SO4 (2 mL) in ethanol (15 mL). The mixtures were refluxed for 4-10 h, while progress of the reaction was monitored through thin layer chromatography. When reaction was completed, solvent was evaporated on a rotary evaporator under reduced pressure and residue was washed with hot hexane. Resulting compounds were crystallized by ethanol to give title compounds in moderate to good yields. |
|
With sulfuric acid; In ethanol;Reflux; |
General procedure: Synthesis of triazole Schiff?s bases was reportedpreviously [44]. Briefly, 4-arylimino-1,2,4-triazoles (1-14)and 3-arylimino-1,2,4-triazoles (15-23) were synthesized byrefluxing <strong>[584-13-4]4-amino-1,2,4-triazole</strong>s, or 3-amino-1,2,4-triazoles(2 mM) with equimolar amounts of substituted benzaldehydeand H2SO4 (2 mL) in ethanol (15 mL) for 4-10 h. Reactionprogress was monitored by TLC under UV light at 254 and365 nm or via exposure to iodine vapours. After completionof reaction, the solvent was vaporised under reducedpressure on a rotary evaporator. Resulting compounds werewashed with hexane and crystallized from ethanol to obtain apure compounds. |
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