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ABSTRACT:
Aminomethylation of benzotriazole was carried out by treating benzotriazole with formaldehyde and N-sec.butyl 4-aminosalicylic acid. The resultant compound was designated as 1-(4-caroxy-3-hydroxy-N-sec.butyl phenyl amino methyl) benzotriazole (CSPB). The transition metal complexes of Cu2+ , Co2+, Ni2+, Mn2+and Zn2+ of CSPB have been prepared and characterized by elemental analysis, spectral studies, magnetic moment, molar conductivity and antimicrobial activity.
KEYWORDS: Benzotriazole, N-sec.butyl-4-aminosalicylic acid, metal complexes, spectral studies, magnetic moment, antibacterial and antifungal activity.
INTRODUCTION:
One of the heterocyclic compound say 1-(H)benzotriazole is found as an important heterocyclic compound. It's prime application is as corrosion inhibiters for copper or copper alloys1,2. Ciba Geigy has introduced benzotriazole derivative under the trade name Trinavin-p3. It is applied as an UV light absorber for stabilizing plastics and other organic materials against discoloration determination3. It is also employed as photographic emulsion stabilizer4. In the peptide synthesis it acts in form of an active ester5. The area in which the amino methylation of benzotriazole by using aromatic amine having metal gripping group (i.e ligand) has not been developed. Hence it was thought to undertake such work. With this view, the present author communicated the initial work recently6. In connection of this work the present paper describes the synthesis and characterization of benzotriazole, N-sec.butyl-4aminosalicylic acid clubbed molecule and its metal complexes6-10. The work is illustrated in Scheme-1.
EXPERIMENTAL:
Materials
Benzotriazole was prepared by method reported in literature11. N-sec.butyl-4-aminosalicylic acid was prepared by method reported12,13. All other chemicals used were of analytical grade.
Synthesis of 1-(4-carboxy-3-hydroxy-N-sec.butyl phenyl amino methyl) benzotriazole:
A mixture of 1-H Benzotriazole (0.02 mole), formaldehyde (0.02 mole) and N-sec.butyl-4aminosalicylic acid (0.02 mole) in ethanol (70 ml) was heated under refluxed for 4h. Subsequently ethanol was distilled off and the lump mass obtained. It was triturated with petroleum ether (40-60 °C). The solid designated as CSPB was isolated and dried in air. Yield was 60%. It's m.p. was 198°C. (Uncorrected).
Synthesis of metal complexes of CSPB:
Formation of CSPB metal complexes:
The Cu2+' Co2+, Ni2+,Mn2+, and Zn2+ metal ion complexes of CSPB have been prepared in a similar manner. The procedure is as follow.
To a solution of CSPB (0.1 mole) in ethanol-acetone (1:1) mixture (25 ml), 0.1 N KOH solution was added drop wise with stirring. The pasty precipitates were...