CS276206B6 - N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof - Google Patents

Abstract

N- [2- (1,0-undecenoyloxy) ethyl] -N, N, N-alkyldimethylammonium bromides formula CH 2 = CH- (CH 2) 8 -COO- (CH 2) 2 -P (CH 3) 2 R Br wherein R represents an alkyl chain having a number of atoms carbon 2 to 14 and the methods of their preparation, which consists in the reaction of the N, N-dimethylaminoethyl ester of 10-undecenoic acid with 1-bromoalkane in polar at different temperatures and during different reaction times.

Description

The invention relates to N- [2- (10-undecenoyloxy) ethyl] -N, N, N-alkyldimethylammonium bromides of the general formula

CH ₂ = CH- (CH ₂ ) _g -COO- (CH ₂ ) ₂ -N (CH ₃ ) ₂ R Br I.

wherein R represents an alkyl chain having 2 to 14 carbon atoms and a process for their preparation.

Organic ammonium salts, which contain at least one long alkyl chain in their molecule, represent a group of compounds with a marked biological, in particular antimicrobial, effect. Due to this property, they have found industrial use, such as very effective disinfectants, auxiliaries in the pharmaceutical, textile, heavy industry, etc. They are used in organic synthesis, for example in the preparation of unsaturated compounds such as interfacial catalysts, etc.

They are prepared in various ways, of which the most commonly used method is the reaction of haloalkanes or dialkyl sulfates with the corresponding tertiary amines. The reaction is carried out under various conditions, yielding ammonium salts of variable purity and in variable yields. The reaction is most often carried out in ethanol, nitromethane, benzene or toluene.

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 18 to 22 hours, producing products of high purity and in high yields.

The examples show the preparation process according to the invention as selected compounds of the invention, in addition to yield and elemental analysis, melting points, Rj values (IMHCl-acetone 1: 9 developing system, Oragendorf reagent detection in Munier modification) and antimicrobial activities detected by the dilution assay directly in the culture medium. Efficacy is reported as the minimum MIC inhibitory concentration in μg / ml against Staphylococcus aureus, Esherichia coli and Candida albicans. The antimicrobial activity of the compounds according to the invention is a new property hitherto unknown for these compounds. The examples illustrate but do not limit the scope of the method used.

Example 1

To 0.06 mol of 10-undecenoic acid, N, N-dimethylaminoethyl ester dissolved in 12 ml of dry methyl cyanide at room temperature is added 0.06 mol of 1-bromohexane. The reaction mixture is heated at 100 DEG C. for 18 hours. After cooling and distilling off the solvent, the crude product, N- [2- (10-undecenoyloxy) ethyl] -N, N, N-hexyldimethylammonium bromide, is recrystallized to constant melting point from dry acetone. . The product has m.p. 98-99 ° C. Elemental analysis% (calculated / found): C: 59.91 / 59.93, H: 10.30 / 10.31; N: 3.33 / 3.05; yield BB% of theory; Rf = 0.36; MIC 8, 70, 40.

Example 2

The procedure is the same as in Example 1, except that 1-bromooctane was used in the reaction, and the solvent was dry methanol. The bath temperature was 80 ° C and the reaction time was 20 hours. The product N- [2- (10-undecenoyloxy) ethyl] -N, N, N-dimethyloctylammonium bromide mp 144-146 ° C; Elemental Analysis% (calculated / found): C: 61.53 / 61.77; H: 10.55 / 10.59; H: 3.12 / 3.13; exhaust 75% of theory; R _f : 0.39; MIC 4, 50, 20.

CS 276 206 B6

Example 3

The procedure is the same as in Example 1, 1-bromodecane was used in the reaction, the solvent was methyl cyanide, the reaction time was 22 hours, and the reaction temperature was 70 ° C. The product N72- (10-undecenoyloxy) ethyl] -N, N, N-decyldimethylammonium bromide mp 164-165 ° C; Elemental Analysis% (calculated / found): C: 62.82 / 63.27; H: 10.75 / 10.83; N: 2.93 / 2.91; yield 85 theory; R _F : 0.41; MIC 3, 70, 30.

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

Claims (2)

PATENT CLAIMS N- [2- (10-uncenoyloxy) ethyl] -N, N, N-alkyldimethylammonium brody of general formula I., wherein R represents an alkyl chain with a number of carbon atoms from 2 to 14. ® © CH ₉ = CH- (CH ₉ ) „- C00- (CH„) „- N (CH,) ₉ R Βγ (I) Z Z o Z Z> Z 2. A process for the preparation of N- [2- (10-undecenoyloxy) ethyl] -N, N, N-alkyldimethylammonium bromides of the formula I according to item 1, characterized in that N, N-dimethylaminoethyl ester of 10-undecenoic acid of the general formula I is reacted. formulas CH "= CH- (CH") "- COO- (CH") "- N (CH ₇ )" (II) Z 1 o Z Z 2 z with 1-bromoalkanes of the general formula R-Br, where R is the same as in point 1, in a dry methanol or methyl cyanide medium in the temperature range of 70 to 100 ° C for 18 to 22 hours.