2-{bis[(1,5-dimethyl-1H-pyrazol-3-yl)methyl]amino}ethanol

Mohamed El Kodadi, Fouad Malek, Rachid Touzani and Abdelkrim Ramdani*.

Laboratory of Chemistry Organic-Physics, Department of Chemistry, Faculty of Sciences, University Mohammed The First, BP 524-60 000 Oujda, Morocco.

E-mail: [email protected]

Received: 5 January 2003 / Accepted: 19 November 2003 / Published: 24 February 2004 

Keywords: tripod, pyrazole, tridentate, ligand.

To a mixture of 3-chloromethyl-1,5-dimethylpyrazole 1 [1] (6g, 41mmol) and sodium carbonate (17g, 160mmol) in 150 mL of acetonitrile was added slowly 2-aminoethanol 2 (1.25g, 20.5 mmol). The mixture was stirred under reflux for 6h [2, 3]. The solid material (Na₂CO₃, NaCl) was filtered and the filtrate was concentrated under reduced pressure. The residue was purified on alumina column with (CH₂Cl₂/EtOH: 97/3) as eluent to give the title compound 3 as yellowish solid (4.56g, 80%).

Melting Point = 64-66°C (CH₂Cl₂/EtOH).

Rf =0.6 (alumina -CH₂Cl₂/EtOH : 97/3).

IR (KBr, cm^-1): 3380(OH), 2980(CH), 1680(C=C), 1560(C=N), 1460, 1400, 1300, 1160, 1140, 1070, 1040, 990, 800.

¹H NMR (200 MHz, CDCl₃) d ppm: 5.95(s, 2H, HPz); 3.70(s, 6H, N-CH₃);

3.65(s, 4H, Pz-CH₂); 3.55(t, 2H, O-CH₂, J=5.12Hz); 2.66(t, 2H, N-CH₂, J=5.12Hz);

2.21(s, 6H, 2CH₃).

¹³C NMR (50MHz, CDCl₃) d ppm: 11.65(Pz-CH₃); 36.26(N-CH₃); 51.70(CH₂-CH₂-N); 54.89(CH₂-OH); 59.34(Pz-CH₂-N); 105.55(PzC-H); 139.65(PzC=N); 148.72(PzC-N).

MS[EI]: m/z = 277; 246; 217; 168; 138; 109(100%); 95; 56; 42.

References

1.      Yahyi, A. Thesis, University Mohammed The First, Oujda, Morocco, 1991.

2.      Malek, F.; Persin, M.; Ramdani, A.; Sarrazin, J.; Zidane, I., New J. Chem.,2002, 26, 876.

3.      Radi, S.; Ramdani, A.; Lekchiri, Y.; Morcellet, M.; Crini, G.; Morcellet, J.; Janus, L. Eur. Polym. J., 2000, 36,1885.

Sample Availability: Available from the Authors.

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