CS237747B1 - N7 (2-alkanoylamido) ethyl] -dodacyldimethylammonium bromides and their preparation - Google Patents

Abstract

The invention relates to N-/(2-alkanoylamido)-ethyl/-doacyldiethylammonium bromonium of the general formula _ CH, )l 3 R-C0-NH-(CH2)2- V-C12H25 CH3 Brc where R represents an alkyl chain with the number of carbon atoms from 2 to 12 and spThe person of their preparation, which consists in the reaction (2-DimethylaminoethylJalkanoylamide with 1-bromododecene in a polar environment at different temperatures and during different reaction times. The organic ammonium salts prepared in this way show antimicrobial as well as surface-active properties.

Description

(54) N7 (2-alkanoylamido) ethyl / dodacyldimethylammonium bromides and process for their preparation

The present invention relates to N - [(2-alkanoylamido) ethyl] -dacetyldiethylmonium bromonium of the formula

CH ^{3 III}

R-C0-NH (CH _{2) 2} N ^C 12 ^H 25

CH ₃

R ^c wherein R znpčí alkyl chain having a carbon number of 2 to 12, and their preparation, which comprises reacting (2-1-dimetylaminoetylJalkanoylamldu bromdodekénom in a polar medium at different temperatures and for different reaction times.

The organic ammonium salts thus prepared exhibit antimicrobial as well as surfactant properties.

237747 2

The present invention relates to N - [(2-alkanoylamido) -ityl] -dodecyldimethylammonium bromides of the general

CH,

R-CO-KH (CH _{2) 2} -®KC, ^2H 25

(Ιθ (I)

CH wherein R is an alkyl chain having a carbon number of 2 to 12 and a method of preparation. Similar compounds of similar Structural Patterns are, for example:

r-coo- (ch ₂ ) ₂ -n (ch ₃ ) ₂ c ₁₂ to ₂₅ Bj £,

Φ z)

CH ₃ -COO- (CH ₂ ) ₂ -N (CH ₃ ) ₂ R B 1 ',

C 1 -COO- (CH ₂ ) ₂ -N (CH ₃ ) ₂ C ₁₂ H ₂₅ N 2.

It is known that organic ammonium salts containing at least one long alkyl chain in their molecule represent a group of compounds with significant biological effects and disinfectant properties. Therefore, they have found use in many industries such as: food, paper, textile, exploit! as corrosion inhibitors, building auxiliaries, pharmaceuticals, cosmetics and the like.

They use! also in organic synthesis, e.g. in the preparation of unsaturated compounds such as interfacial catalysts and the like. Their antibacterial effects are used for disinfection in hospitals as well as in schools, municipal facilities, food wholesalers, etc.

Organic ammonium salts are prepared in a variety of ways, most often by reacting halogenated derivatives of a different structure with the corresponding tertiary amines under various reaction conditions. Usually, products of variable purity and fluctuating yield are produced.

The process according to the invention has the advantage that the reaction can be carried out in methanol or methyl cyanide under various conditions of temperature and reaction time, thereby obtaining products of high purity and in high yields.

In the examples, the spflsob preparation of the invention and the selected compounds which are the subject of the invention, both are characterized by selected compounds and is designated the IR spectral characteristics (measured in nujol mull, cm ^'- ^) except yield and melting point, and anti-microbial activity detected by dilution assay directly in the culture medium. Efficacy is reported as the minimum inhibitory concentration (MIC) in pg / ml on Staphylococcus aureus, Escheriohia coli, Candida albicans.

The antimicrobial activity of the compounds of the invention is a novel property not yet known from these compounds.

Examples illustrate !, but. do not limit the scope of the method used

Example ,

To 0.025 mol of (2-dimethylaminoethyl) hexanoylamide dissolved in 5 ml of dry methyl cyanide at room temperature was added 0.025 mol of 1-bromododecane. The reaction mixture was heated at 00 ° C for 16 h. After cooling and distilling off the solvent, the crude product, N - [(2-hexanoylamido) ethyl] -dodecyldimethylammonium bromide, is recrystallized to constant melting point from dry acetone. Mp 84-85 ° C; Elemental Analysis% (calculated / found): C 60.61 / 60.20; H, 10.81 / 10.87; M 6.43 / 6.21; yield 92% of theory; IR (3,237, 3,197, -) _{c = 0} 1,668 (Amid I), 1,531 (Amid II), _CN

274 (Amid III); MIC 5, 30, 8.

Example 2

The procedure was the same as in Example 1 except that (2-dimstylaminoethyl) octanoylamide was used for the reaction, the solvent was methyl cyanide, the reaction time was 20 hours, the reaction temperature was 85 ° C. The product N - [(2-octanoylamido) ethyl] -dodecyldimethylammonium bromide had m.p. mp 88-90 ° C; Elemental Analysis% (calculated / found): C 62.13 / 62.13;

H 11.08 / 11.23; N, 6.04 / 6.02; yield 88% of theory; 3δ 3,237, 3,197, ^ _{c = 0} (Amid I)

662, γ- _{c (JH} (Amid II) 1531, _CN (Amid III) 1274; MIC 4, 30, 3).

Example 3

The procedure was identical to that of Example 1, using (2-dimethylaminoethyl decanoylamide, methanol, reaction temperature 75 ° C, reaction time 18 hours) The product N - [(2-decanoylamido) ethyl] -dodecyldimethylammonium bromide had a tt of 93- 94 ° C, elemental analysis% (calculated / found): C 63.47 / 63.42, H 11.27 / 11.09;

N, 5.69 / 5.55; yield 80% of theory; 2δ 2 237, 3 197, _{c = 0} (Amide I) 1 662, (Amide II) 1 531, y _CN (Amide III) 1 274; MIC 10, 200.5.

All of the compounds thus prepared were white, slightly hygroscopic, soluble in polar, insoluble in non-polar solvents. In addition to elemental analysis, spectral ones were also identified.

Claims (2)

EXAMPLE To 0.025 mol of (2-dimethylaminoethyl) hexanoylamide dissolved in 5 ml of dry methyl cyanide at room temperature was added 0.025 mol of 1-bromododecane. The reaction mixture was heated at 100 ° C for 16 hours. After cooling and distilling off the solvent, the crude product, N - [(2-hexanoylamido) ethyl] dodecyldimethylammonium bromide, overlaps to a constant melting point of dry acetone. Mp 84-85 ° C; elemental analysis% (calculated): C 60.61 / 60.20; H, 10.81 / 10.87; M, 6.43 / 6.21; yield 92% of theory; IR 3 237, 3 197, -) c = 0 1668 (Amide I), 1531 (Amide II), CN 1 274 (Amide III); MIC 5, 30, 8. EXAMPLE 2 The procedure is the same as in Example 1 except that (2-dimethylaminomethyl) octanoylamide was used, the solvent was cyanide, the reaction was for 20 hours, the temperature was 85 ° C. The product N - ((2-octanoylamido) ethyl) -dodecyldimethylammonium bromide had m.p. 88-90 ° C; elemental% analysis (calculated): C 62.13 / 62.13; H, 11.08 / 11.23; N, 6.04 / 6.02; yield 88% of theory; ΐδ 3 237, 3 197, c = 0 (Amide I) 1 662, yc (JH (Amide II) 1 531, 1 CN (Amide III) 1 274; MIC 4, 30, 3. Example 3 The procedure is identical with the procedure of Example 1, (2-dimethylaminoethyl decanoylamide, methanol, 75 [deg.] C., 18 hours) was used. N - [(2-decanoylamido) ethyl] dodecyldimethylammonium bromide had a m.p. elemental analysis% (calculated / found): C 63.47 / 63.42, H 11.27 / 11.09, N 5.69 / 5.55, yield 80% of theory, δδ 2 237, 3 197, c = (Amide I) 1662, (Amide II) 1531, CN (Amide III) 1174, MIC 10, 200, 5. All of the compounds thus prepared were white, slightly hygroscopic, soluble in polar, insoluble in non-polar solvents. OF THE INVENTION 1. N - [(2-alkanoylamido) ethyl] -dodecyldimethylammonium bromides of formula I, CH, R10-CO-NH- (CH2) 2- NC, 2H25CH, Br (I) where R is an alkyl chain of carbon atoms ka 2 to 12 2. A process for the preparation of N - ((2-alkynoylamido) ethyl) dodecyldimethylammonium bromides of general formula (I) according to claim 1, characterized in that (2-dimethylaninoethyl) -alkanoyl amide of the formula R-CO-NH- (CH2) 2 is reacted -N (CH 3) 2 (II) wherein R represents an alkyl chain having from 2 to 12 carbon atoms, with 1-bromododecane in dry cyanide or methanol at 75-100 ° C, for 16-20 hours.