CS276206B6 - N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof - Google Patents
N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof Download PDFInfo
- Publication number
- CS276206B6 CS276206B6 CS905152A CS515290A CS276206B6 CS 276206 B6 CS276206 B6 CS 276206B6 CS 905152 A CS905152 A CS 905152A CS 515290 A CS515290 A CS 515290A CS 276206 B6 CS276206 B6 CS 276206B6
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- CS
- Czechoslovakia
- Prior art keywords
- ethyl
- alkyldimethylammonium
- bromides
- reaction
- undecenoyl
- Prior art date
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract description 8
- 150000001649 bromium compounds Chemical class 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 9
- -1 N, N-dimethylaminoethyl ester Chemical class 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960002703 undecylenic acid Drugs 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 230000035484 reaction time Effects 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WMYMGQIVIVCVRQ-UHFFFAOYSA-N dimethyl(octyl)azanium;bromide Chemical compound Br.CCCCCCCCN(C)C WMYMGQIVIVCVRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SRESKMPUIWAGML-UHFFFAOYSA-N n,n-dimethyldecan-1-amine;hydrobromide Chemical compound Br.CCCCCCCCCCN(C)C SRESKMPUIWAGML-UHFFFAOYSA-N 0.000 description 1
- VDABETAUSGGGPE-UHFFFAOYSA-N n,n-dimethylhexan-1-amine;hydrobromide Chemical compound Br.CCCCCCN(C)C VDABETAUSGGGPE-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N- /2 -(1.0-undecenoyloxy)etyl/-N,N,N-alkyldimetylamoniumbromidy všeobecného vzorca CH2=CH-(CH2)8-C00-(CH2)2-íP(CH3)2R Br kde R značí alkylový reíazec s počtom atómov uhlika 2 až 14 a sposob ich přípravy, ktorý spočívá v reakcií N,N-dimetyl-aminoetylesteru kyseliny 10-undecénovej s 1-brómalkánom v polárnom prostředí při různých teplotách a počas různej reakčnej doby.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
Vynález sa týká N-/2-(10-undecenoyloxy)ety1/-N,N,N-alkyIdimetylamóniumbromidov všeobecného vzorca ® ©The invention relates to N- [2- (10-undecenoyloxy) ethyl] -N, N, N-alkyldimethylammonium bromides of the general formula
CH2=CH-(CH2)g-COO-(CH2)2-N(CH3)2R Br I.CH 2 = CH- (CH 2 ) g -COO- (CH 2 ) 2 -N (CH 3 ) 2 R Br I.
kde R značíalkylový retazec s počtom atómov uhlíka 2 až 14 a sposob ich přípravy.wherein R represents an alkyl chain having 2 to 14 carbon atoms and a process for their preparation.
Organické amoniové soli, ktoré obsahujú vo svojej molekule, najmenej jeden dlhý alkylový retazec, predstavujú skupinu zlúčenín s výrazným biologickým, predovšetkým antimikróbnym účinkom. Pře tuto vlastnost našli priemyselné použitie, ako velmi účinné dezinficienciá, pomocné látky vo farmaceutickom, textilnom, íažkom priemysle a pod.. Používajú sa v organickej syntéze, například při přípravě nenasýtených zlúčenín ako medzifázové katalyzátory, ató..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.
Pripravujú sa rěznymi spósobmi, z ktorých najčastejšie používanou metodou je reakcia halogénalkánov, připadne dialkylsulfátov s příslušnými terciárnymi amínmi. Reakcia sa uskutečňuje v róznych podmienkach, pričom sa získavajú amoniové soli variabilnej čistoty a vo variabilných výtažkách. Reakcia sa najčastejšie uskutečňuje v etanole, nitrometáne, benzene alebo toluene.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.
Sposob podía vynálezu má tú výhodu, že sa reakcia mflže uskutečnil v metanole alebo metylkyanide pri roznych teplotách počas 18 až 22 hodin, pričom vznikajú produkty vysekej čistoty a vo vysokých výíažkoch.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.
V příkladech je uvedený sposob přípravy podía vynálezu, ako vybrané zlúčeniny, které sú predmetom vynálezu, okrem výtažku a prvkovej analýzy sú uvedené teploty topenia, Rj- hodnoty (vyvýjacia sústava IMHCl-acetón 1:9, detekcia Oragendorfovým činidlom v Muniérovej modifikácii) a antimikróbne aktivity zistené dilučným testom priamo v kultivačnom médiu. Účinnost je uvedená ako minimálna inhibičná koncentrácias MIC v /jg/ml voči Staphylococcus aureus, Esherichia coli a Candida albicans. Antimikróbna aktivita zlúčenín, ktoré sú predmetom vynálezu, je vlastnost nová, doteraz u týchto zlúčenín neznáma. Příklady ilustrujú, ale neobmedzujú rozsah použitej metody.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.
Příklad 1Example 1
K 0,06 mol Ν,Ν-dimetylaminoetylesteru kyseliny 10-undecénovej rozpuštěnému v 12 ml suchého metylkyanidu za laborato.rnej teploty sa přidá 0,06 mol 1-brómhexánu. Reakčná zmes sa zahrieva 18 hodin při teplete 100 C. Po ochladení a oddestilovaní rozpúštadla sa surový produkt, kterým je N-/2-(10-undecenoyloxy)etyl/-N,N,N-hexyldimetylamóniumbromid prekryštalizujc do konštantnej teploty topenia zo suchého acetonu. Produkt má t.t. 98 až 99 °C. Elementárna analýza % (vypočitané/zistené): C: 59,91/59,93, H: 10,30/10,31; N: 3,33/3,05; výtažok BB % teorie; R^-: 0,36; MIC 8, 70, 40.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.
Příklad 2Example 2
Pracovný postup je ten istý ako v příklade 1, s tým rozdielom, že do reakcie sa použil 1-brómoktán, rozpúšíadlom bol suchý metanol. Teplota kúpeía bola 80 °C a reakčný čas 20 hodin. Produkt N-/2-(10-undecenoyloxy)etyl/-N,N,N-dimetyloktylamóniumbromid mal t.t. 144 až 146 °C; elementárna analýza % (vypočitané/zistené): C: 61,53/61,77; H: 10,55/10,59; H: 3,12/3,13; výfažok 75 % teorie; Rf: 0,39; MIC 4, 50, 20.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 B6CS 276 206 B6
Příklad 3Example 3
Pracovny postup je zhodný s postupom uvedeným v příklade 1, do reakcie sa použil 1-brómdekán, rozpúšíadlom bol metylkyanid, reakčný čas bol 22 hodin a reakčná teplota 70 °C. Produkt N72-(10-undecenoyloxy)etyl/-N,N,N-decyldimetylamóniumbromid mal t.t. 164 aý 165 °C; elementárna analýza % (vypočítané/zistené): C: 62,82/63,27; H: 10,75/10,83; N: 2,93/2,91; výíažok 85 teorie; RF: 0,41; MIC 3, 70, 30.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.
Všetky takto připravené zlúčeniny boli biele krystalické, mierne hydroskopické zlúčeniny, rozpustné v polárných a nerozpustné v nepolárných rozpúšíadlách. Okrem elementárnej analýzy boli identifikované aj spektrálnými metodami.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.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS905152A CS515290A3 (en) | 1990-10-23 | 1990-10-23 | N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS905152A CS515290A3 (en) | 1990-10-23 | 1990-10-23 | N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS276206B6 true CS276206B6 (en) | 1992-04-15 |
| CS515290A3 CS515290A3 (en) | 1992-04-15 |
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| CS905152A CS515290A3 (en) | 1990-10-23 | 1990-10-23 | N-/2(10-undecenoyl)ethyl/-n,n,n-alkyldimethylammonium bromides and process for preparing thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9796662B2 (en) | 2010-10-25 | 2017-10-24 | Stepan Company | Esteramines and derivatives from natural oil metathesis |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19510813A1 (en) * | 1995-03-24 | 1996-09-26 | Degussa | Activators for peroxo compounds and agents containing them |
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1990
- 1990-10-23 CS CS905152A patent/CS515290A3/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9796662B2 (en) | 2010-10-25 | 2017-10-24 | Stepan Company | Esteramines and derivatives from natural oil metathesis |
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| Publication number | Publication date |
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| CS515290A3 (en) | 1992-04-15 |
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