CS226934B1 - N-(2-(p-tert.butylbenzoyloxy)ethyl)-n,n-dimethylalkylam - Google Patents

Description

The invention relates to N- [2- (p-tert-butylbenzoyloxy) ethyl] -N, N-dimethylammonium bromides of the formula

where

R represents an alkyl chain having a number of carbon atoms of 8 to 16 and a process for their preparation.

Organic ammonium salts containing at least one long alkyl chain in their molecule represent a group of compounds with a pronounced biological, especially antimicrobial, effect. In spite of this, they have found use in practice as very effective disinfectants, auxiliaries in the pharmaceutical, textile, heavy industry and the like. They are also used in organic synthesis e.g. in the preparation of unsaturated compounds such as interfacial catalysts, etc.

They are prepared in a variety of ways, the most commonly used method for the reaction of halonalkanes or dialkyl sulfates with the corresponding tertiary amines. The reaction takes place in different environments, especially polar, but reactions in non-polar solvents, at different temperatures and during different reaction times are also known. Usually, products are obtained in a variable yield of variable purity.

The process according to the invention has the advantage that the reaction can be carried out in methanol or methyl cyanide at different temperatures, for 8 to 24 hours, whereby high purity products are obtained in high yields.

The examples illustrate the preparation process of the present invention as well as selected compounds of the present invention. These are characterized and the antimicrobial activity against Staphylococcus aureus, Escherichia coli and Candida albicans as minimum inhibitory concentration (MIC) in µg / ml is also reported. The antimicrobial activity of the compounds of the present invention is a novel property not previously known for these compounds.

The examples illustrate but do not limit the scope of the method.

EXAMPLE

To 0.1 mol of (2-dimethylaminoethyl) - p-tert-butylbenzoate dissolved in 10 ml of dry methyl cyanide was added 0.1 mol of 1-bromooctane at room temperature and the mixture was heated at 100 ° C for 8 hours. of the solvent, the crude product, N- [2- (p-tert-butylbenzoyloxy) ethyl] -N, N-dimethyloctylammonium bromide, is recrystallized to constant melting point from dry acetone, m.p. 117-118 ° C;

elemental analysis (calculated% / found%):

C 62.36 / 62.74, H 9.10 / 9.35, N 3.17 / 3.00; yield 80% of theory;

MIC: 3, 40, 9.

Example 2

The procedure is the same as in Example 1 except that 1-bromodecane, solvent methanol, bath temperature 80 ° C, reaction time 16 hours was used in the reaction. The product N- [2- (p-tert-butylbenzyloxy) ethyl] 4

-Ν, Ν-dimethyldecylammonium bromide had t. t. 150-151 ° C;

elemental analysis (calculated% / found ° / o):

C 63.89 / 64.17, H 9.44 / 9.67, N 2.98 / 2.70; yield 81% of theory;

MIC: 3, 5, ^_2:;

EXAMPLE 1 a d 3

The procedure is identical to that of Example 1, 1-bromododecane was used, the solvent was methyl cyanide, the reaction time was 24 hours, the reaction temperature was 50 ° C. The product N- [2- (p-tert-butylbenzoyloxy) ethyl] -N, N-idimethyldodecylammonium bromide had mp 154-156 ° C;

elemental analysis (calculated% / found%):

C 64.86 / 65.20, H 9.70 / 10.00, N 2.81 / 2.95; yield 83% of theory;

MIC: 3, 60, 2.

All of the compounds thus prepared were white crystalline, slightly hygroscopic compounds, soluble in polar and insoluble in non-polar solvents. In addition to elementary analysis, they were also identified by spectral methods.

Claims (2)

OBJECT OF THE INVENTION 1. N- [2- (p-tert-Butylbenzoyloxy) ethyl] -N, N-dimethylalkylammonium bromides of formula q ch ₃ CH ₃ R ₃ wherein with 1-bromoalkane of the general formula R is an alkyl chain of 8 to 16 carbon atoms. 2. The method of preparing compounds of the formula · as in 1, characterized in that the chloride, (2-dimethylamino-ethyl) -p-tert-butylbenzoate formula _CH3 Chy-C- O ch ₃ co-^ n -nc. R = Br, where R is the same as in point 1, in a dry methyl cyanide or methanol medium between 50 and 100 ° C, for 8 to 24 hours. and