CS216447B1 - Alkyldimethyl-p-tert. butylbenzylammonium bromides and their method of preparation - Google Patents

Abstract

The invention relates to alkyldimethyl-p-tert.butylbenzylammonium bromides of the general formula where R denotes an alkyl chain with the number of carbon atoms from 8 to 16 and the method of their preparation, which consists in the reaction of p-tert.butylbenzyl bromide with the corresponding alkyldimethylamine in a neutral environment. The compounds prepared in this way show significant antimicrobial and surface-active properties

Description

The invention relates to alkyldimethyl-p-tert. butylbenzylammonium bromides of the general formula i

wherein R is a linear alkyl chain having a number of carbon atoms of 8 to 16 and a process for their preparation.

Organic ammonium salts with at least one long alkyl chain are known to exhibit significant biological effects (e.g., antimicrobial, muscarinic, curareform) as well as surface-active properties. Therefore, they find use as disinfectants, detergents, pharmaceuticals, auxiliaries for pharmaceutical industry but also in organic synthesis e.g. as interfacial catalysts or in the preparation of unsaturated compounds.

Most of the industrially used ammonium salts are prepared by reaction of the respective targets. of amines with haloalkanes under various reactions conditions with variable yield. The process of the invention utilizes the p-tert reaction. of butylbenzyl bromide with alkyldimethylamine in a polar environment to give high purity products.

The compounds of the invention are novel substances not previously described in the chemical literature. They have so far unknown effects on microorganisms. In terms of disinfectant activity, these substances are comparable to commercially used disinfectants of this type and the most effective ones outperform these substances in their activity (Ajatin, Septonex).

The examples illustrate a process for the preparation of selected compounds of the invention and their characterization, indicating their antimicrobial activity expressed as the minimum inhibitory concentration (MIC) in pg / ml per strain: Staphylococcus aureus, Escherichia eoli and Candida albicans. The examples do not limit the scope of this method. and

Example 1

To 0.1 mol of dimethyloctylamine dissolved in 10 ml of dry methanol is added 0.1 mol of p-tert at room temperature. butylbenzyl bromide. The reaction mixture was heated at 100 ° C for 4 hours. After cooling, the methanol is distilled off and the crude product is octyldimethyl-p-tert. the butylbenzylammonium bromide is recrystallized to a constant melting point from dry acetone. The product has a t. mp 89-91 ° C; Elemental analysis (calculated / found): C = 65.60 / 66.27

H = 10.35 / 9.97 N = 3.60 / 3.48; yield 57% of theory; MIC: 10; 60; 20th

Example 2

The procedure is the same as that in Example 1 except that dodecyldimethylamine was used in the reaction and the solvent was ethanol. The product, dodecyldimethyl-p-tert. butylbenzylammonium bromide, m.p. t. Mp 109-111 ° C; elemental analysis (calculated / found): C = 68.21 / 68.01 H = 10.54 / 10.46 N = 3.18 / 3.34; yield 66% of theory; MIC: 5; 30; Second

Example 3

The procedure is identical to that of Example 1 except that hexadecyldimethylamine was used in the reaction. The product, hexadecyldimethyl-p-tert. butylbenzylammonium bromide had 1.1. 70-72 ° C; elemental analysis (calculated / found): C = 70.23 / 69.97 H = 10.97 / 10.92 N = 2.82 / 3.03; yield 57% of theory; MIC: 3; 90; 0.8.

All the compounds thus prepared were white crystalline, low hygroscopic substances, soluble in polar and insoluble in non-polar solvents. Besides the analysis, they were also identified by spectral methods.

Claims (2)

SUBJECT MATTER Alkyldimethyl-p-tert-butylbenzylammonium bromides of the formula wherein R is an alkyl chain having from 8 to 16 carbon atoms. 2. A process for the preparation of compounds of formula (I) as defined in claim 1, characterized in that p-tert is reacted. butylbenzyl bromide of formula with an alkyldimethylamine of the formula N -R ui, wherein R is the same as in 1, in a dry methanol or ethanol medium at a temperature range of 20 to 100 ° C. 216447