CS277139B6 - N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof - Google Patents
N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof Download PDFInfo
- Publication number
- CS277139B6 CS277139B6 CS905436A CS543690A CS277139B6 CS 277139 B6 CS277139 B6 CS 277139B6 CS 905436 A CS905436 A CS 905436A CS 543690 A CS543690 A CS 543690A CS 277139 B6 CS277139 B6 CS 277139B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ethyl
- undecenoylamino
- bromides
- preparation
- preparing
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-(2-(10-undecenoylamino)etyl]-Ν,N,N-alkyladimetylamóniumbromidy a spósob ich přípravy. Riešenie sa týká N-[2-(10-undecenoylamino)etyl]-Ν,N,N-alkyldimetylamóniumbromidov všeobecného vzorca I CH2=CH-(CH2)8-CO- -NH-(CH2)2-ří®(CH3)2R Bl© (i), kde R značí alkylový reťazec s počtom atómov uhlíka 2 až 14 a spósob ich pripravy, ktorý spočívá v reakcií Ν,Ν-dimetylamidoetylaesteru kyseliny 10-undecénovej s l-brómalkánom v polárnom prostředí pri roznych teplotách a počas róznej reakčnej doby. Takto připravené organické amóniové soli vykazujú anitimikróbne, ako aj povrchovoaktívne vlastnosti a preto sú použitelné ako detergenty, napr. s dezinfekčným účinkom.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
Vynález sa týká N-[2-(10-undecenoylamino)etyl]-N,N,N-alkyldimetylamóniumbromidov všeobecného vzorca I ch2=ch-(ch2)8-co-nh-(ch2)2-n ® (ch3)2 R Br θ I, kde R znáči alkylový retazec s počtom atómov uhlíka 2 až .14a spósobu ich přípravy.
Je známe, že organické amóniové soli, ktoré obsahujú vo svo-jej molekule najmenej jeden dlhý alkylový retazec, představujúskupinu zlúčenín s výraznými biologickými účinkami a s dezinfekč-nými vlastnostami. Preto našli použitie v mnohých odvetviachpriemyslu, ako napr. potravinářsky, papierenský, textilný, využí-vajú sa ako inhibitory korózie, pomocné látky vo farmácii, kozme-tike, atd.. Používájú sa aj v organickej syntéze, například pripríprave nenasýtených zlúčenín ako medzifázové katalyzátorya pod.. Ich antibakteriálne účinky sa využívajú na dezinfekciutak v nemocniciach, ako aj v školách, komunálnych zariadeniacha inde.
Organické amóniové soli sa pripravujú róznymi spósobmi,z nich najčastejšie reakciou halogenderivátov rožnej štruktúrys příslušnými terciárnymi amínmi za rozličných reakčných podmie-nok. Vznikájú obvykle produkty variabilnej čistoty a v kolísavomvýtažku. Spósob podlá vynálezu má tú výhodu, že sa reakcia móžeuskutočnit v metanole, alebo metylkyanide, za róznych podmienokteploty a reakčného času, pričom sa získajú produkty vysokéjčistoty a vo vysokých výtažkoch. Zlúčeniny podlá vynálezu sú lát-ky nové, doteraz v chemickéj literatúre neopísané a zistili sau nich doteraz neznáme účinky na mikroorganizmy.
Podstatou spósobu přípravy N-[2-(10-undecenoylamino)etyl]-N,Ν,Ν-alkyldimetylamóniumbromidov všeobecného vzorca I. Podlá vyná-lezu je, že sá nechá reagovat Ν,Ν-dimetylaminoetylamid kyseliny10-undecénovej všeobecného vzorca II ch2=ch-(ch2)8-co-nh-(ch2)2-n(ch3)2 II, s 1-brómalkánmi všeobecného vzorca R-Br, kde R značí to isté akov bode 1, v prostředí suchého metylkyanidu alebo metanole v roz-medzí teplot 75’ až 90 ’C počas 18 až 22 hodin.
V príkladoch je uvedený spósob přípravy podlá vynálezu, akoaj charakterizácia vybraných zlúčenín, uvádza sa ich antimikróbnaaktivita zistená dilučným testom priamo v kultivačnom médiu.Účinnost je uvedená ako minimálna inhibičná koncentrácia (MIC)v μg/ml voči Staphylococcus aureus, Escherichia coli a Candidaalbicans. Ďalej sú uvedené ich Rp hodnoty (vyvíjacia sústava 1M HCl-acetón 1:9, detekcia Dragendorfovým činidlom v Muniérovejmodifikácii). Příklady ilustrujú, ale neobmedzujú rozsah použitejmetody.
CS 277139 B6 2 Příklad 1 K 0,025 mol Ν,Ν-dimetylaminoetylamidu kyseliny 10-undecéno-vej rozpuštěného v 5 ml suchého metylkyanidu za laboratórnejteploty sa přidá 0,025 mol 1-brómhexánu. Reakčná zmes sa zahrieva18 hodin pri teplote 90 ’C. Po ochladení a oddestilovaní rozpú-štadla sa surový produkt, ktorým je N-[2-(10-undecenoylami-no)etyl]-N,N,N-hexyldimetylamóniumbromid, prekryštalizuje do kon-stantně j teploty topenia zo suchého acetonu. Produkt má teplotutopenia 32° až 33 °C; elementárna analýza % (vypočítané/zistené):C: 60,20/59,95; H: 10,34/10,42; N; 6,69/6,47; výtažok 85 % teo-rie; Rp; 0,28; MIC 9, 200, 70. Příklad 2
Pracovný postup je ten istý ako v příklade 1, s tým rozdie-lom, že do reakcie sa použil 1-brómoktán, rozpúštadlom bol metyl-kyanid, reakčný čas 20 hodin, reakčná teplota 85 °C. Produkt N--[2-(10-undecenoylamino)etyl]-N,N,N-dimetyloktylamóniumbromid malt.t. 41,5° až 43 "C; elementárna analýza % (vypočítané/zistené);C; 61,80/61,29; H: 10,60/10,39; N; 6,27/5,91; vý€ažok 81 %teorie; Rp: 0,33; MIC 1, 60, 50. Příklad 3
Pracovný postup je zhodný s postupom ako v příklade 1, doreakcie sa použil 1-brómdekán, rozpúštadlom bol metanol, reakčnáteplota 75 °C, reakčný čas 22 hodin. Produkt N-[2-(10-undecenoyl-amino)etyl]-N,N,N-decyldimetylamóniumbromid mal t.t. 83,5° až84 °C; elementárna analýza % (vypočítané/zistené): C: 63,08/63,60; H; 10,80/11,20; N: 5,89/5,94; výtažok 79 % teorie; RF;0,36; MIC 1, 50, 9. Všetky takto připravené zlúčeniny boli biele mierne hygro-skopické látky, rozpustné v polárných, nerozpustné v nepolárnýchrozpúštadlách. Okrem elementárnej analýzy boli identifikované ajspektrálnými metodami.
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)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS905436A CS277139B6 (en) | 1990-11-06 | 1990-11-06 | N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS905436A CS277139B6 (en) | 1990-11-06 | 1990-11-06 | N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CS543690A3 CS543690A3 (en) | 1992-05-13 |
CS277139B6 true CS277139B6 (en) | 1992-11-18 |
Family
ID=5399273
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS905436A CS277139B6 (en) | 1990-11-06 | 1990-11-06 | N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof |
Country Status (1)
Country | Link |
---|---|
CS (1) | CS277139B6 (en) |
-
1990
- 1990-11-06 CS CS905436A patent/CS277139B6/en unknown
Also Published As
Publication number | Publication date |
---|---|
CS543690A3 (en) | 1992-05-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0172656B1 (en) | Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof | |
US3320229A (en) | Complexes of guanidines with completely halogenated acetones | |
SU682096A3 (en) | Microbicidal preparation | |
Clifton et al. | N1-(substituted) pantothenamides, antimetabolites of pantothenic acid | |
Krapcho et al. | Syntheses and pharmacological activity of compounds related to the antidepressant, 5-(2-dimethylaminoethyl)-2, 3-di-hydro-2-phenyl-1, 5-benzothiazepin-4 (5H)-one (thiazesim). III | |
US2624757A (en) | Substituted aralkyl alkylene diamino di acetic acids and salts | |
DE68918910T2 (en) | Iodopropargyl monoesters of dicarboxylic acid anhydrides and their use as antimicrobial agents. | |
SU663267A3 (en) | Method of fighting insects, ticks and nematodes | |
US3574837A (en) | New schift's bases,and their use as agricultural pesticides | |
CS277139B6 (en) | N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof | |
CS276206B6 (en) | N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof | |
CS237747B1 (en) | N-/(2-alkanoylamid)ethyl/-dodecyldimethylamoniumbromide and method of their preparation | |
US3457310A (en) | Hexahaloxylidides | |
US3721679A (en) | 1,3-disubstituted-2-trichloromethyl-5-imino-4-imidazolidinones | |
US3342829A (en) | Bis-quaternary salts of triamines and process for preparing them | |
CS216447B1 (en) | Alkydimethyl-p-terc.butylbenzylammoniumbromides and method of preparation the same | |
CS226934B1 (en) | N-(2-(p-tert.butylbenzoyloxy)ethyl)-n,n-dimethylalkylam | |
CS233421B1 (en) | N-(2-alkanoyloxy)atyl)dodecyldimethyl-ammoniumbromides | |
CS226935B1 (en) | N-(2-(p-tert.butylphenoxyacetoxy)ethyl)-n,n-dimethylalkyl-ammonium bromides and method of preparing same | |
US4965395A (en) | P-oxybenzoic acid compounds | |
Sacco Jr et al. | The Synthesis of N, N-Bis-(β-diethylaminoethyl)-amine and Some N-Substituted Alkanesulfonamides | |
FI63749C (en) | NEW ENAMINERS OF WOOL AER MELLAN PROCESSING OF PHARMACEUTICAL ACTIVE SUBSTITUTES N- (1-ALKYL-2-PYRROLIDINYLMETHYL) | |
JPS61500118A (en) | Phenylguanidines | |
EP0144420B1 (en) | Guanidated aminophosphonic acid compounds | |
CS229092B1 (en) | N,n'-bis/alkyldimethyl/-3-aza-3-/p-tert.butyl-benzyl/-1,5-pentanediammonium dibromides and method of preparing same |