Next Article in Journal
Synthesis, Physical Characterization, Antibacterial and Antifungal activities of a novel bis(3-((E)-1-(2-hydroxyphenyl)ethylideneamino)phenyl)methanone
Previous Article in Journal
1,1’-dibenzyl-5,5’-diphenyl-3,3’-bipyrazole
Article Menu

Export Article

Molbank 2006, 2006(4), M483; doi:10.3390/M483

Short Note
N,N-bis[(1,5-dimethylpyrazol-3-yl)methyl]para-toluidine
Laboratoire de Chimie Organique Physique, Département de Chimie, Faculté des Sciences, Université Mohamed Premier, BP 524, 60000, Oujda, Maroc
*
Author to whom correspondence should be addressed.
Received: 24 October 2005 / Accepted: 15 January 2006 / Published: 1 June 2006
Keywords:
Tripod; pyrazol; ligand; tridentate
Molbank 2006 m483 i001
The mixture of para-toluidine 1 (0.535 g, 5 mmol), 3-chloromethyl-1,5-dimethylpyrazol 2 (1.44 g, 10 mmol) and sodium carbonate (4.24 g, 40 mmol) in acetonitrile (50 mL) was refluxed for three hours [1,2,3]. The solvent was removed at reduced pressure. The residue was purified through a silica column (CH2Cl2) to give the product 3 (726 mg, 45 % yield) as a white solid.
Melting point: 98 - 100°C (CCl4)
IR (KBr, cm-1): 3020 (ν=C-H); 2960 (νC-H, CH3); 2920 (νC-H, CH2); 2875 (νC-H, N-CH3); 1620 (νC=N); 1530 (νC=C); 1430; 1390 (δC-N); 1340; 1235; 1185; 940; 800 (δ=C-H); 780.
1H-NMR (CDCl3, 300 MHz): d= 6.94 (d, 2 H, H2’, J = 8.4 Hz); 6.78 (d, 2 H, H3’, J = 8.4 Hz); 5.85 (s, 2 H, C4-H); 4.46 (s, 4 H, N-CH2-pz); 3.69 (s, 6 H, N-CH3); 2.19 (s, 3 H, CH3-C6H4 ); 2.16 (s, 6 H, C5-CH3).
13C-NMR (CDCl3, 75 MHz): d= 149.72 (C3); 143.50 (C1’); 139.51(C5); 129.85 (C3’); 125.42 (C4’); 113.54 (C2’); 104.51(C4); 49.34 (N-CH2-pz); 36.25 (N-CH3); 20.62 (CH3-C6H4); 11.65 (C5-CH3).
MS (EI), m/z: 323 (5.4 %); 228 (0.4 %); 214 (100 %); 109 (24.5 %); 91 (4.4 %); 77 (0.5 %); 56 (4.9 %); 40 (3.5 %).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

  1. Bouabdallah, I.; Ramdani, A.; Zidane, I.; Touzani, R. Molbank 2005, M 397.
  2. Bouabdallah, I.; Ramdani, A.; Zidane, I.; Touzani, R.; Eddike, D.; Radi, S.; Haidoux, A. J. Chem. Res. 2005, 242–244.
  3. Malek, F. Thèse de Doctorat d’Etat; Faculté des Sciences: Oujda, Maroc, 1995. [Google Scholar]
  • Sample Availability: Available from MDPI.
Molbank EISSN 1422-8599 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top