CS233421B1 - N-(2-alkanoyloxy)atyl)dodecyldimethyl-ammoniumbromides - Google Patents

Abstract

N - ((2-alkanoyloxy) ethyl) - -dodecyldlaetylaaoaiuBbroaids general where R is an alkyl chain and the number of atoms Carbon Dioxide 2 to 12a and their Preparation Process which consists of reacting the (2-diaethylaainoethyl) alkanoate and 1-broadodecanoa in the polar environment at various temperatures and conditions different reaction times. The organic astronomy thus prepared salts exhibit both anti-microbial and superficial properties actively properties.

Description

The present invention relates to N - [(2-alkanoyloxy) ethyl] dodecyldimethylammonium bromide in the form

CH,

R - C 0 0 - (CH ₂ ) ₂ - N - C ₁₂ H ₂₅ Br

CH, (I), wherein R is an alkyl chain with a number of carbon atoms of 2 to 12 and may be readily prepared. A similar compound of formula Eu like žtruktúrneho include CH-COO-ICH ^ j R ^ gÓlKCH ® Br, C ₆ H ₅ COO (CH _{2) 2} R (CH _{3) 2} C ₁₂ H ₂₅ Br ^θ, (0Η _{3) 3} -0-Ο ₆ Η ₄ -00Ο- (0Η ₂ ) ₂ ^ Κ0Η ₃ ) 2Β Br ®.

The organic ammonium salts containing at least one long alkyl chain in their molecule represent a group of compounds and a remarkable biological, predominantly antimicrobial effect. For this property has experienced industrial use, such as very effective desiccants, excipients in pharmaceutical, textiles, heavy industry, etc. ·. They are also used in organic synthesis, e.g. in the preparation of unsaturated compounds such as copper phase catalysts and the like.

The most commonly used method for the reaction of haloalkanes or dlalkylaulphates with the appropriate terelamyl amine is reacted under various conditions, whereby they obtain ammonium salts of aarlabile purity and in variable variability. Most often, the reactions are carried out in water, ethanol, nitromethane, but also in benzene and toluene.

The process according to the invention has the advantage that the reaction can be carried out in methanol weakly methyl cyanide at different temperatures for 12 to 22 hours, except for products of high purity and in high yields.

In the examples, the method of processing according to the invention is shown as 1 selected compounds of the invention. These are characterized and the anti-mlobacter activity of Staphylococcus aureus, Escherichia cell and Candida albicane as a minimum inhibitory concentration (HIC) in µg / ml is also reported.

The anti-fungal activity of the compounds of the invention is a novel property which is unknown to these compounds.

Examples Illustrate but do not limit the scope of the method used.

EXAMPLE

To 0.1 mol of (2-diethylaminoethyl) hexanoate dissolved in 10 [mu] l of dry methyl cyanide is added at room temperature and 0.1 mol of 1-bromododecane is added. The reaction mixture was heated at 100 ° C for 12 hours. After cooling and distilling off the solvent, the crude product, which is N - [(2-hexanoyloxy) ethyl] dodecyldimethylemmonium bromide, recrystallizes to constant melting point with dry acetone. The product has m.p. Mp 166-168 ° C; elehentric analysis (calculated / zwittered): C 60.89 / 60.55; H 10.68 / 10.57? H, 3.23 (3.06), 80% yield; MIC 3,20,5.

Example 2

The procedure is the same as in case 1 except that (2-dimethylaminoethyl) octanoate was used in the reaction, the solvent was methanol, the bath temperature was 85 ° C and the reaction time was 18 hours. The product N - / (2-octanoyloxy) ethyl (-dodecyldimethylammonium bromide) had mp 179.5-181 ° C, elemental analysis (calculated / found): C 61.99 / 62.23, H 10.64 / 10.82; M 3.01 / 2.99; yield 91% of theory; MIC 7.30.9.

Example 3

The procedure was identical to that of Example 1, but using (2-diaethylamino-ethyl) decanoate, the reagent hol ethyl ethyl cyanide, reaction time was 22 hours, reaction temperature 60 ° C. The product N - [(2-dodecanoyloxy) ethyl] -dodecyldimethylammonium bromoBldmal m.p. 182.5 ° C; Alemantam Analysis (calculated / found): C 63.34 / 63.16; H, 11.04 / 11.15; 84% yield; MIC 6,80,30.

a.

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

Claims (2)

OBJECT IN YNA CLIMBING 1. N - [(2-alkanoyloxy) ethyl] -dodecyldimethylammonium bromides of the general formula I, CH, Br ^θ (I) R - C 0 O - (CH ₂ ) ₂ - N - C ₁₂ H ₂₅ ' ^H 3 wherein R represents an alkyl chain having from 2 to 12 carbon atoms. 2. A process for the preparation of N - [(2-alkanoyloxy) ethyl] -dodecyldimethylammonium bromoald according to the general formula (I) according to claim 1, characterized in that the (2-dimethylalaminoethyl) alkanoate is reacted in general formula II, V R - COO - (CH ₂ ) ₂ - M (CH ₃ ) ₂ (II), where R stands for the same as in point 1, with 1-bromodecane in dry methanol or methyl cyanide at temperatures ranging from 60 to 100 ° C for 12 up to 22 hours.