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

N-(2-alkanoyloxy)atyl)dodecyldimethyl-ammoniumbromides Download PDF

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CS233421B1
CS233421B1 CS184683A CS184683A CS233421B1 CS 233421 B1 CS233421 B1 CS 233421B1 CS 184683 A CS184683 A CS 184683A CS 184683 A CS184683 A CS 184683A CS 233421 B1 CS233421 B1 CS 233421B1
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Prior art keywords
alkanoyloxy
ethyl
general formula
ammoniumbromides
atyl
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CS184683A
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Czech (cs)
Slovak (sk)
Inventor
Imrich Csiba
Ivan Lacko
Arpad Nagy
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Imrich Csiba
Ivan Lacko
Arpad Nagy
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Priority to CS184683A priority Critical patent/CS233421B1/en
Publication of CS233421B1 publication Critical patent/CS233421B1/en

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Abstract

Vynálss sa týkj N-/(2-alkanoyloxy)etyl/- -dodecyldlaetylaaoaiuBbroaidov všeobecného vsorca kde R značí alkylový reťatec a počtoa atoaov uhlíka 2 až 12a apOsobu ich přípravy, ktorý spočívá v reakc^i (2-diaetylaainoetyl)alkanoátu a 1-broadodekánoa v polárnoa prostředí pri rOsnych teplotách a počaa rčznej reakčnej doby. Takto připravená organická aaóniová soli vykazuji antiaikrobálne ako aj povrchovo aktivně vlastnosti.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

Vynález ea týká N-/(2-alkanoyloxy)etyl -dodecyldimetylamóniumbroaldov vžeobeeného vsorcaThe present invention relates to N - [(2-alkanoyloxy) ethyl] dodecyldimethylammonium bromide in the form

CH,CH,

R - C 0 0 - (CH2)2 - N - Cj2H25 BrR - C 0 0 - (CH 2 ) 2 - N - C 12 H 25 Br

CH, (I), kde R značí alkylový reťasec a počtom atomov uhlíka 2 až 12 a spdaobu leh pripravy. Obdobná zlúčeniny podobného žtruktúrneho vzorca eú například: CHj-COO-ÍCH^gÓlKCH^jR Br ®, C6H5-COO-(CH2)2^(CH3)2C12H25 Br θ , (0Η3)3-0-Ο6Η4-00Ο-(0Η2)2^Κ0Η3)2Β 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 ®.

Organické amónlové soli, ktéré obsahujú vo svojej molekule najmenej jeden dlhý alkylový reťasec, představujú skupinu slúSenín a výrasným biologickým, predovžetkým antlmlkróbnym účinkom. Pre tuto vlastnost nažil prlemyselné použitie, ako velmi účinné deslňficienčlé, pomocné látky vo farmaceutickou, textllnom, ťažkom prlemysle apod·. Používajú sa aj v organické j syntéze napr. pri príprave nenasýtených zlúčenín ako medslfásové katalysátory atá..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.

Pripravujú sa rOsnyml spOaobml s ktorých je najčastejšie používaná metoda reakcia halogénalkánov připadne dlalkylaulfátov s prí služnými terelámyml amínmli Reakcia sa uskutočňuje v rOsnych podmienkach, pričom ea získávájú amónlové soli aarlabllnej čistoty a vo varlabilnýeh výťažkoch. Hajčastejžle sa reakcie uskutočňujú vo vodě, etanole, nitrometáne, ale aj v benséne a toluéne.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.

Spdsob podía vynálezu má tú výhodu, že sa reakcia mdže uekutočnit v metanole slabo metylkyanide pri rdsnych teplotách počas 12 až 22 hodin, prlčqm vsnikajd produkty vysokéj čistoty a vo vysokých výťažkoch.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.

V príkladoch je uvedený spdsob drípravy podía vynálesu ako 1 vybrané slúčenlny, ktoré sú predmetom vynálezu. Tieto sú charakterizované a je uvedená aj antlmlkróbna aktivita vdčl Staphylococcus aureus, Escherichia cell a Candida albicane ako minimálně lnhiblčná koncentrácia (HIC) v/ug/ml.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.

Antlmlkróbna aktivita zlúčenín, ktoré sú predmetom vynálesu je vlastnost nová, doteras u týchto zlúčenín neznáma.The anti-fungal activity of the compounds of the invention is a novel property which is unknown to these compounds.

Příklady Ilustrujú, ale neobmedsujú rozsah použitej metody.Examples Illustrate but do not limit the scope of the method used.

PřikladlEXAMPLE

K 0,1 mol (2-dlaetylamlnoetyl)hexánoátu rozpuštěného v 10 al suchého metylkyanidu sa laboratorněj teploty ea přidá 0,1 mol 1-brómdodekánu. Reakčné směs sa zahrieva 12 hodin pri teplote 100 °C. Po oehladení a oddestilovani rospúžťadla ta, surový produkt ktorým Je N-/(2-hexanoyloxy)etyl/-dodécyldlmetylemóniumbromld prekryžtalisuje do konštantnej teploty tppenia so suchého acetonu. Produkt má t.t. 166 až 168 °C; elehentárna analýsa (vypočítané/ /zietené): C 60,89/60,55; H 10,68/10,57? H 3,23/3,06} výťažok 80 % teorie; MIC 3,20,5.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.

Příklad 2Example 2

Pracovný postup je ten istý ako v případe 1, s tým rosdieloa, že do reakcie ta použil (2-dimetylaminoetyl)oktanoát, rospúžťadlom bol metanol, teplota kúpela bola 85 °C a reakčný čas 18 hodin. Produkt N-/(2-oktanoyloxy)etyl(-dodecyldimetylamónlumbromld mal t.t. 179,5 až 181 °C; elementárna analýza (vypočítané/zistené): C 61,99/62,23; H 10,64/10,82; . M 3,01/2,99? výťažok 91 % teorie; MIC 7,30,9.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.

Příklad 3Example 3

Pracovný postup je shodný s postupem příkladu 1, do reakcie sa použil(2-diaetyláminoetyl)dekanoét, rospúStadlom hol aetylkyanid, reakčný Sas bol 22 hodin, reakčné teplota 60 °C. Produkt N-/(2-dodekanoyloxy)etyl/-dodecyldimetylamónlumbroBldmal t.t. 182,5 °C; alemantáma analýza (vypočítané/zistené): C 63,34/63,16; H 11,04/11,15» výtažok 84 % teorie; MIC 6,80,30.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 .a.

VSetky takto připravená zlúčeniny boli biele krystalická, mieme hygroakopieká zlúčeniny, rozpustná v polárných a nerozpustná v nepolárných rozpúStadléch. Okrem elementérj nej analýzy holi identifikovaná aj spektrálnými metodami.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)

PREDMET V YNA LEZUOBJECT IN YNA CLIMBING 1. N-/(2-alkanoyloxy)etyl/-dodecyldimetylamóniumbromidy vSeobecnáho vzorca I, CH,1. N - [(2-alkanoyloxy) ethyl] -dodecyldimethylammonium bromides of the general formula I, CH, Br θ (I),Br θ (I) R - C 0 0 - (CH2)2 - N - C12H25 ' ÍH3 kde R značí alkylový retazec s po8tom atómov uhlíka 2 ež 12.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. Spdsob přípravy N-/(2-alkanoyloxy)etyl/-dodecyldimetylamóniumbroaldov vSeobecnáho vzorca I., podXa bodu 1, vyznačujúci sa tým, Se ea nechá reagovat (2-dimetylaainoetyl)alkanoát vSeobecnáho vkorca II, V2. 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 - C O O - (CH2)2 - M (CH3)2 (II), kde R značí to istá ako v bode 1, s 1-brómdekánom v prostředí suchého metanolu alebo metylkyanidu v rozmedzí tepldt 60 až 100 °C počas 12 až 22 hodin.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.
CS184683A 1983-03-17 1983-03-17 N-(2-alkanoyloxy)atyl)dodecyldimethyl-ammoniumbromides CS233421B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110818577A (en) * 2019-11-07 2020-02-21 南京威尔生物化学有限公司 Preparation method and application of glyphosate granule auxiliary agent with high drug effect

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110818577A (en) * 2019-11-07 2020-02-21 南京威尔生物化学有限公司 Preparation method and application of glyphosate granule auxiliary agent with high drug effect

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