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
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- 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
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- ethyl
- undecenoylamino
- bromides
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 11
- -1 10-undecenoylamino Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 10
- 150000001649 bromium compounds Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract description 2
- 230000000249 desinfective effect Effects 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 150000003842 bromide salts Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 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
- 230000002289 effect on microbe Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 239000012454 non-polar solvent Substances 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 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
- 229960002703 undecylenic acid Drugs 0.000 description 1
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- 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 |
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| 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 |
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| CS (1) | CS277139B6 (en) |
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1990
- 1990-11-06 CS CS905436A patent/CS277139B6/en unknown
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| Publication number | Publication date |
|---|---|
| CS543690A3 (en) | 1992-05-13 |
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