Molbank 2005, M398

N’,N’-bis[(3,5-dimethyl-1-pyrazolyl)methyl],N,N-dimethyl-para-phenylenediamine.

Ibrahim Bouabdallah*, Ismail Zidane, Rachid Touzani and Abdelkrim Ramdani

Laboratoire de Chimie Organique Physique, Département de Chimie, Faculté des Sciences,

Université Mohamed Premier, BP 524, 60000, Oujda, Maroc

e-mail : Bouabdallah@sciences.univ-oujda.ac.ma . [email protected]

Received: 18 March 2004 / Accepted: 25 March 2004 / Published: 1 July 2005

Keywords: pyrazol, ligand.

The mixture of N,N-dimethyl-para-phenylenediamine 2 (136 mg, 10 mmol) and 1-hydroxy-methyl-3,5-dimethylpyrazol 1 (252 mg, 20 mmol) in CH₃CN (20 mL), was stirred at room temperature for five days[1, 2]. The organic layer was dried over Na₂SO₄, filtered and concentrated at reduced pressure. The residue was purified by recrystallysation in dichloromethane-diethylether to give product 3 as a black solid (300 mg, 85 %).

Melting point: 88-90 °C (dichloromethane-diethylether: 1/1).

IR (KBr, cm^-1): 2990 (CH₃); 1580 (C=C); 1510 (C=N).

¹H-NMR (300 MHz, CDCl₃): δ= 6.68 (2H, d, H¹, J = 8.9 Hz); 6.53 (2H, d, H², J = 8.9Hz); 5.68 (2H, s, CH pyrazolyl); 5.30 (4H, s, CH₂); 2.83 (6H, s, N-CH₃); 2.19 (6H, s, CH₃); 1.85 (6H, s, CH₃).

¹³C-NMR (300 MHz, CDCl₃): δ= 148.63; 147.96; 140.23; 136.38; 126.32; 113.59; 106.74; 66.15; 41.22; 13.96; 11.18.

EI-MS (70 eV, m/z): 352; 243; 215; 148; 109; 96; 77; 54; 42.

References and Notes:

1. Driessen, W. J. R.. Neth. Chem. Soc. 1982, 101, 441.

2. Bouabdallah, I.; Zidane, I and Ramdani, A. Rapport de DESA . Faculté des sciences, Oujda, Maroc, 2001.

Sample Availability: Available from the Authors.