To a solution of 3-phenyl-5-methylpyrazole 1 [1] (7.11 g, 45 mmol) in ethanol (60 mL) was added formaldehyde 2 (3.85 g, 45 mmol, 35 %) and the mixture was refluxed for 90 minutes [2,3]. The reaction was continued at room temperature for 12h. The mixture was concentrated at reduced pressure. The residue was purified by recrystallization to afford the product 3 as a white solid.
Yield: 4.65 g, 55 %.
Melting point: 145-146 °C (CH3COCH3)
IR (KBr, cm−1): 3100 (νO-H); 2920 (CH3); 1540 (νC=C); 1430, 1380, 1350, 1280 (δO-H); 1200, 1190, 1065, 1060, 1000, 970, 945, 790, 720.
1H-NMR (200 MHz, CDCl3): δ= 7.76 (m, 2H, CH ph, o-H); 7.23 (m, 3H, CH ph, m-H, p-H); 6.41 (s, 1H, CH pz); 5.61 (s, 2H, CH2); 2.45 (s, 3H, CH3).
MS (EI, 70eV; m/z): 188; 158; 143; 128; 117; 104; 90; 77; 63; 51; 40.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3References and Notes:
- Ali, S. S.; Ashraf, C. M.; Younas, M.; Ehsan, A. Pak. J. Sci. Ind. Res. 1993, 36, 502–510.
- Driessen, W. J. R.. Neth. Chem. Soc. 1982, 101, 441.
- Bouabdallah, I.; Zidane, I; Ramdani, A. Rapport de DESA; Faculty of Sciences: Oujda, Maroc, 2001. [Google Scholar]
- Sample Availability: Available from MDPI.
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