CS233421B1 - N7 (2-alkanoyloxy) atyl / * dodecyldimatyl ammonium bromides and their method of preparation - Google Patents

N7 (2-alkanoyloxy) atyl / * dodecyldimatyl ammonium bromides and their method of preparation 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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ethyl
preparation
general formula
alkanoyloxy
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CS184683A
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Czech (cs)
Slovak (sk)
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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
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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.The invention relates to N-/(2-alkanoyloxy)ethyl/--dodecyldlaethylaoaiuBbroides of the general formula where R is an alkyl chain and the number of carbon atoms is 2 to 12, and the method of their preparation, which consists in the reaction of (2-diethylaainoethyl)alkanoate and 1-broadodecano in a polar environment at different temperatures and the beginning of the reaction time. The organic aaonium salts prepared in this way show antimicrobial as well as surface-active properties.

Description

233421 2233421 2

Vynélea sa týká N-/(2-alkanoyloay)etyl -dodecyldlaetylaaóniuabroaldov všeobecného vaorea CH, R - C 0 O - (CH2)2 - N - Cj2H25 Br CH, (I), kde R znaSÍ alkylový retaaec a poSto· atoaov uhllka 2 až 12 a spSsobu leh přípravy. ObdobnísldSenlny podobného ttruktdrneho vaorea ad například: CHj-COO-tCH^g^lUCH^jR Br ®,C6H5-COO-(CH2)2^(CH3)2C12H25 Br θ , (CH3)3-C-C6H4-COO-(CH2)2^í(CH3)2R Br ® .The invention relates to N - ((2-alkanoyloay) ethyl-dodecyl-diethylalanine-abrasionate of the general formula CH, R - C 0 O - (CH 2) 2 --N - C 2 H 25 Br CH, (I) where R denotes an alkyl chain and carbon atoms 2 to 12 and the method of preparation. Similar to a structure-like structure and for example: CH 3 -COO-CH 2 gCH 2 CH 2 R 5 R 5, C 6 H 5 -COO- (CH 2) 2 (CH 3) 2 C 12 H 25 Br θ, (CH 3) 3 -C 6 C 4 H 4 -COO- (CH 2) ) 2 ^ (CH 3) 2 R Br ®.

Organické aaónlové aoll, ktéré obsahu jd vo svojej molekule najaenej jeden dlhý alky-lový retaaec, představujd skupinu aldSenín a výraanýa biologický·, predovéetkýa antiaikrób-nya dSlnkoa. Pre tuto vlastnost naéll prieayselné poutitle, ako veial dSlnné deslňficiendlá,poaocné látky vofaraaceutlckoa, textilnoa, tetko* prleaysle apod·. Poutlvajd sa aj v orga-nické j syntéae napr. prl príprave nenasýtenýoh aldSenín ako aedslfésové katalyaátory etá..The organic aonic aoll, which contains a long alkyl chain in its molecule, is a group of aldenesin and biosynthetic, antioxidant and antioxidant. For this property, nails tend to be dense, such as dense fillers, snacks in pharmaceuticals, textiles, tattoos, and the like. Also, in the organic synthesis, for example, the preparation of unsaturated alkanesin as allylphosphate catalysts et al.

Prlpravujd sa rOanyal spdsobal a ktorých je najSastejSle poutívaná aetoda reakci·halogénalkánov připadne dlalkylsulfátov a prísluSnýal terelámyal ealnal; Reakci· sauakutoSnuje v r&anych podaletdcach, pričoa aa aíakavajd aaónlové aoll aarlabllnej čistotya vo varlabilných výtažkoch. HajSastejSle sa reakci· uskutoSňujd vo vod·, etanole, nitro-aetáne, ale aj v benséne a toluéne.The preparation is made to act and which is most closely bound by the reaction and the haloalkanes or alkylsulfates and the corresponding terealmeal; The reaction is ascertained in the form of analaric purity and purity in varlabile extracts. The reaction is carried out in water, ethanol, nitro-aethane, but also in bensene and toluene.

SpOsob podlá vynálezu aá td výhodu, Se sa reakci· adie uskutoSnit v metanole aleboaetylkyanide prl rfianych teplotách poSaa 12 at 22 hodin, prlSq* vanikajd produkty vyaokejSistoty a vo vysokých výtatkoch. V příkladech je uvedený spOaob Orípravy pódia vynáleau ako 1 vybrané sldSenlny, ktoráad predaetoa vynáleau. Tleto ad oharakterlsované a je uvedená aj antlalkróbna aktivita vSSlStaphylococcua aureus, Escherichia cell a Candida albicana ako alniaálna lnhiblSná koncentrá-cla (MIC) v/ug/ml.The process according to the invention has the advantage that the reaction is carried out in methanol or ethyl cyanide at temperatures of from 12 to 22 hours, by means of high purity and high yield products. In the examples, the Stage Adjustment Process is presented as 1 selected slds which inventes the present invention. This is characterized and the anti-cranial activity of SS1Staphylococcua aureus, Escherichia cell and Candida albicana as alnia inhibition concentrations (MIC) in µg / ml is also reported.

Antlalkróbna aktivita aldSenín, ktoré ad predaetoa vynáleau je vlastnost nová, dote-raa u týchto aldSenín neanáaa. Příklady lluatrujd, ale neobaedaujd rozsah poutitej metody. Přikladl K 0,1 mol (2-dlmetylaalnoetyl)hexánoátu roapuateného v 10 al suchého aetylkyanlduaa laboratorněj teploty aa přidá 0,1 aol 1-brómdodekánu. ReakSná snes sa aahrieva 12 hodinprl teplot· 100 °C.Po ochládání a oddestilovani rospdStadla aa, surový produkt ktorý· jeN-/(2-hexanoyloxy)etyl/-dodécyldlaetylaaóniuabroald prekryStaliauje do konBtantnej teplotytppenia ao suchého acetonu. Produkt aá t.t. 166 at 168 °C; elehentárna analýsa (vypočítané//zlatěné): C 60,89/60,55} H 10,68/10,57} H 3,23/3,06} výtatok 80 % teorie} MIC 3,20,5. Příklad 2The anti-cellular activity of aldenesin, which in the present invention is a novel feature, is not readily available. Examples of lluatrujd, but not the scope of an engaging method. EXAMPLE 1 To 0.1 mol of (2-dimethylanyl ethyl) hexanoate roapuated in 10 .mu.l of dry ethyl acetate and laboratory temperature and 0.1 .mu.l of 1-bromododecane is added. The reaction temperature is 12 hours at 100 DEG C. After the solvent is distilled off and distilled, the crude N - [(2-hexanoyloxy) ethyl] -dodecyl-ala-lauroic acid is recrystallized to a constant temperature and dry acetone. The product was m.p. 166 at 168 ° C; electroanalysis (calculated // gold): C 60.89 / 60.55} H 10.68 / 10.57} H 3.23 / 3.06} 80% theory} MIC 3.20.5. Example 2

Pracovný postup je ten lstý ako v případe 1, a týa rosdieloa, te do reakeie ta poulil(2-diaetylaainoetyDoktanoát, roapdStadloa bol metanol, teplota kdpela bole 85 °C a reakBnýSas 18 hodin. Produkt N-/(2-oktanoyloxy)etyl(-dodecyldiaetylaaóniuabroBld aal t.t. 179,5 at181 °C; elenentárna analýza (vypodítané/ziatené): C 61,99/62,23} H 10,64/10,82; . M 3,01/2,95}výtažek 91 % teorie; MIC 7,30,9.The working procedure is the same as in case 1, and the method is used for the preparation (2-diaethylaaino-acetonitrile, methanol was methanol, the temperature was 85 ° C and the reaction time was 18 hours. The product N - [(2-octanoyloxy) ethyl] -dodecyldiaethylaluminum bisabboldal m.p. 179.5 at 181 ° C; elenent analysis (calculated / counted): C 61.99 / 62.23} H 10.64 / 10.82; M 3.01 / 2.95} yield 91% theory, MIC 7.30.9.

Claims (2)

3 233421 Příklad 3 Pracovný postup je shodný s postupoa příkladu 1, do reakeie sa použil(2-diaetyláal-noetyl)dekanoát, rozpúSťadloa hol aetylkyanid, reakSný Sas hol 22 hodin, reakSná teplota60 °C. Produkt N-/(2-dodekanoyloxy)etyl/-dodecyldlaetylaaónluabroBld aal t.t. 182,5 °C;eleaentáma analýza (vypoSítané/sistené): C 63,34/63,16; H 11,04/11,15; výtaiok 84 %teorie; MIC 6,80,30. TSetky takto připravené xlúSenlgy holi biele krystalické, ‘aleme hygroskoplekéslúčenlny, rozpustné v polárných a nerozpustné v nepolárných rozpúStadlách. Okrea eleaentár- j nej analýzy holi Identifikované aj spektrálnými metodami. PŘED li ET V Y N A LEZU 1. N-/(2-alkanoyloxy)etyl/-dodecyldinetylaaónluabroaidy všeobecného vzorca I,CH, Br θ (I), R - C 0 0 - (CH2)2 - N - C12H25' ÍH3 kde R značí alkylový retazec s počtom atóaov uhlíke 2 až 12.EXAMPLE 3 The working procedure is the same as in Example 1, using (2-diaethylaluminum ethyl) decanoate, solvent and ethyl cyanide, reacting with 22 hours, temperature 60 ° C. The product N - [(2-dodecanoyloxy) ethyl] -dodecyldaethylaconluorobenzoate m.p. 182.5 [deg.] C., eleaent analysis (calculated): C 63.34 / 63.16; H, 11.04 / 11.15; extract 84% of theory; MIC 6.80.30. The three thus prepared white crystals are white crystalline, hygroscopic compounds, soluble in polar and insoluble in non-polar solvents. The eleaent analysis of the stick Identified by spectral methods. BEFORE ET VYNA LEZU 1. N - ((2-alkanoyloxy) ethyl) -dodecyldinethylaaloneabaaaa of general formula I, CH, Br θ (I), R - C 0 O - (CH 2) 2 - N - C 12 H 25 'H 3 where R denotes an alkyl chain having from 2 to 12 carbon atoms. 2. SpOsob přípravy N-/(2-alkanoylozy)etyl/-dodecyldiaetylaaóniuabroaldov všeobecnéhovzorca I., podPa hodu 1, vyznačující sa tým, že sa nechá reagovat (2-dimetylamlnoetyl)alka-noát všeobecného vkorca II, V R - C O O - (CH2)2 - & (CH3)2 (II), kde R značí to isté ako v bode 1, s 1-bróadekánom v prostředí suchého metanolu alebo metyl-kyanidu v rozaedzí teplit 60 až 100 °C počas 12 až 22 hodin.2. A process for the preparation of N - [(2-alkanoyloyl) ethyl] -dodecyldiaethylaluminum bromides of general formula (I) according to claim 1, characterized in that (2-dimethylaminoethyl) alkanoate of general formula II, VR - COO - (CH2) is reacted. ) 2 - & (CH 3) 2 (II), wherein R is the same as in 1, with 1-bromoadecane in dry methanol or methyl cyanide at a temperature of 60 to 100 ° C for 12 to 22 hours.
CS184683A 1983-03-17 1983-03-17 N7 (2-alkanoyloxy) atyl / * dodecyldimatyl ammonium bromides and their method of preparation 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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