CS277139B6 - N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof - Google Patents

Abstract

N- (2- (10-undecenoylamino) ethyl] -Ν, N, N-alkyladimetylamóniumbromidy and the method of their preparation. The solution relates to N- [2- (10-undecenoylamino) ethyl] -Ν, N, N-alkyldimethylammonium bromides of formula I CH 2 = CH- (CH 2) 8 -CO- -NH- (CH 2) 2 - (R) (CH 3) 2 R B1 (I) wherein R is an alkyl chain having a carbon number of 2 to 14 and the method of their preparation, which rests in the reaction of Ν, Ν-dimethylamidoethyl acid ester 10-undecene with 1-bromoalkane in polar environment at different temperatures and during a severe reaction time. So prepared the organic ammonium salts exhibit anti-microbial as well as surface-active properties and are therefore useful as detergents, e.g. with disinfecting effect.

Description

CS 277139 B6

The present invention relates to N- [2- (10-undecenoylamino) ethyl] -N, N, N-alkyldimethylammonium bromides of formula I ch 2 = ch- (ch 2) 8-co-nh- (ch 2) 2-n ® (ch 3) 2 R Br I where R denotes an alkyl chain having from 2 to 14 carbon atoms and a process for their preparation.

It is known that organic ammonium salts which contain at least one long alkyl chain in their molecule represent a group of compounds with pronounced biological effects and disinfecting properties. Therefore, they have found use in many industries such as food, paper, textile, corrosion inhibitors, pharmaceutical, cosmetics, etc. They are also used in organic synthesis, such as the preparation of unsaturated compounds as interfacial catalysts. under .. Their antibacterial effects are used for disinfection in hospitals as well as in schools, municipal facilities and elsewhere.

The organic ammonium salts are prepared by various methods, most often by reacting the halide derivatives of the structure with the appropriate tertiary amines under different reaction conditions. Variable purity products and fluctuating yields are usually formed. The process according to the invention has the advantage that the reaction can be carried out in methanol or methyl cyanide, under various temperature and reaction conditions, to obtain products of high purity and high yields. The compounds of the present invention are novel, not previously described in the chemical literature, and have not yet been known to have an effect on microorganisms.

The method of preparation of N- [2- (10-undecenoylamino) ethyl] -N, Ν-alkyldimethylammonium bromides of general formula (I). ch- (ch2) 8-co-nh- (ch2) 2-n (ch3) 2 II, with 1-bromoalkanes of the general formula R-Br, where R is the same as 1, in a dry methyl cyanide or methanol medium between 75 and 90 ° C for 18 to 22 hours.

The examples illustrate the preparation of the present invention, as well as the characterization of the selected compounds, their antimicrobial activity, as determined by the dilution test directly in the culture medium. The following are their Rp values (1M HCl-acetone 1: 9 developing system, Dragendorf reagent detection in Muniermodification). The examples illustrate but do not limit the scope of the method.

EXAMPLE 1 0.025 mol of 1-bromohexane was added to 0.025 mol of 10-undecenoic acid Ν, Ν-dimethylaminoethylamide dissolved in 5 ml of dry methyl cyanide at room temperature. The reaction mixture was heated at 90 ° C for 18 h. After cooling and distilling off the solvent, the crude product, N- [2- (10-undecenoylamino) ethyl] -N, N, N-hexyldimethylammonium bromide, is recrystallized to a constant melting point from dry acetone. The product has a temperature of 32 ° to 33 ° C; elemental analysis% (calculated / found): C: 60.20 / 59.95; H: 10.34 / 10.42; N; 6.69 / 6.47; 85% of theory; Rp; 0.28; MIC 9, 200, 70. Example 2

The working procedure is the same as in Example 1, except that 1-bromoctane was used in the reaction, methyl cyanide was the solvent, the reaction time was 20 hours, the reaction temperature was 85 ° C. The product N - [2- (10-undecenoylamino) ethyl] -N, N, N-dimethyloctylammonium bromide malt. 41.5 ° to 43 ° C; elemental analysis% (calculated / found); C; 61.80 / 61.29; H: 10.60 / 10.39; N, 6.27 / 5.91; to 81% of theory, Rp: 0.33, MIC 1, 60, 50. Example 3

The working procedure was the same as in Example 1, 1-bromodecane was used, the solvent was methanol, the reaction temperature was 75 ° C, the reaction time was 22 hours. The product N- [2- (10-undecenoyl-amino) ethyl] -N, N, N-decyldimethylammonium bromide had a mp of 83.5 ° to 84 ° C; elemental analysis% (calculated / found): C: 63.08 / 63.60; H; 10.80 / 11.20; N: 5.89 / 5.94; 79% of theory; RF, 0.36; MIC 1, 50, 9. All of the compounds thus prepared were white, slightly hygroscopic, soluble in polar, insoluble in non-polar solvents. In addition to elemental analysis, they were also identified by spectral methods.

Claims (2)

Claims 1. N- [2- (10-undecenoylamino) ethyl] -N, N, N-alkyldimethylammonium bromides of formula X., CH 2 = CH- (CH 2) g -CO-NH- ( CH 2) 2 N wherein R is an alkyl chain having from 2 to 14 carbon atoms. 2. A process for the preparation of N- [2- (10-undecenoylamino) ethyl] -N, N, N-alkyldiethylammonium bromides of general formula I according to claim 1, characterized in that N, N-dimethylaminoethylamide is reacted with 10- undecene of the formula CH 2 = CH- (CH 2) g -CO-NH- (CH 2) 2 -N (CH 3) 2 (II) with 1-bromoalkanes of the general formula R-Br, where R is the same as in 1, in a dry environment methyl cyanide or methanol in a temperature range of 75 ° to 90 ° C for 18 to 22 hours. End of document