CS200114B1 - Ammonium salts of esters of 11-aminoundecanoic acid and process for preparing thereof - Google Patents
Ammonium salts of esters of 11-aminoundecanoic acid and process for preparing thereof Download PDFInfo
- Publication number
- CS200114B1 CS200114B1 CS776478A CS776478A CS200114B1 CS 200114 B1 CS200114 B1 CS 200114B1 CS 776478 A CS776478 A CS 776478A CS 776478 A CS776478 A CS 776478A CS 200114 B1 CS200114 B1 CS 200114B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ammonium salts
- esters
- aminoundecanoic acid
- preparing
- dodecyl
- Prior art date
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- 150000003863 ammonium salts Chemical class 0.000 title claims description 5
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- FFJMLWSZNCJCSZ-UHFFFAOYSA-N n-methylmethanamine;hydrobromide Chemical compound Br.CNC FFJMLWSZNCJCSZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 4
- -1 methyl 11-bromo-decanoic acid esters Chemical class 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- HSRFXYHFPDYLPW-UHFFFAOYSA-M CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCC(OC)=O.[Br-] Chemical compound CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCC(OC)=O.[Br-] HSRFXYHFPDYLPW-UHFFFAOYSA-M 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká amániových soli esterov kyseliny 11-aminoundekánovej typu N-dodecyl-(lO-alkoxykarbonyldecyl)dimetylamániumbromidov obecného vzorca I c12H25W2^-{CH2>10-C00R Βιθ (Ι)· kde R značí metyl, etyl, propyl, izopropyl, butyl, pentyl, izopentyl, hexyl a benzyl, a spósobu ich pripravy. Ako je známe, organické amóniové soli obsahujúce vo svojej molekule najmenej jeden dlhý alkylový reťazec, vykazujú okrem iných vlastností aj letálne účinky na rózne kmene mikroorganizmov. U zlúčenin, ktoré sú predmetom vynálezu, sa zistili doteraz neznáme účinky na mikroorganizmy. Uaximálnu antimikrobiálnu aktivitu vykazovali zlúčeniny, kde R bol metyl, benzyl. Predlžovanie reťazca mierne znižuje aktivitu, vetvenie reťazca aktivitu v podstatě neovplyvňuje. Aktivita najúčinnejfiích zlúčenín tohoto typu je zrovnatelná s prostriedkami typu amániových soli používaných v súčasnosti.The present invention relates to ammonium salts of 11-aminoundecanoic acid esters of the N-dodecyl- (10-alkoxycarbonyldecyl) dimethylamanium bromide of the general formula I c 12 H 25 W 2 - ( CH 2> 10 -COOR Βι θ (Ι)) wherein R represents methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, hexyl and benzyl, and a process for their preparation. As is known, organic ammonium salts containing at least one long alkyl chain in their molecule exhibit, among other properties, also lethal effects on different strains of microorganisms. The compounds of the invention have previously been found to have unknown effects on microorganisms. Compounds where R was methyl, benzyl showed maximal antimicrobial activity. Chain lengthening slightly decreases activity, but branching of the chain does not substantially affect activity. The activity of the most potent compounds of this type is comparable to the ammonium salt formulations currently used.
Zlúčeniny, ktoré sú predmetom vynálezu sa pripravujú reakciou dodecyldimetylaminu s prísluňným esterom kyseliny 11-brámundekánovej v prostředí etanolu pri teplote kúpela 100 až 110 °C počas 24 hodin.The compounds of the present invention are prepared by reacting dodecyldimethylamine with the corresponding 11-bromo-decanoic acid ester in ethanol at a bath temperature of 100-110 ° C for 24 hours.
Příklady ilustrujú vyéňie uvedené zlúčeniny a spósob ich pripravy.The examples illustrate the above compounds and the process for their preparation.
200 114200 114
200 114200 114
Příklad 1Example 1
Ekvlmoláma zmea dodecyldimetylamínu a metylesterů kyseliny 11-brómundekánovej sa nechá reagovat v 30 ml etanolu počas 24 hodin pri teplote kúpela 100 až 110 °C. Po oohladení. oddestilovaní rozpúátadla a prekryštalizovaní sa získá N-dodecyl-(10-metoxykarbonyldecyl)dimetylamóniumbromid vo výtažku 35 %; t.t. 41 až 43 °C; Rp=0,54; IČ-spektrálne charakteristiky: 9(CO) 1736. -Q(COC) 1177, -Q (CN) 1105 cm“1 /v nujolovej suspenzi!/.The equimolar mixture of dodecyldimethylamine and methyl 11-bromo-decanoic acid esters is reacted in 30 ml of ethanol for 24 hours at a bath temperature of 100-110 ° C. After check. distilling off the solvent and recrystallization gave N-dodecyl (10-methoxycarbonyldecyl) dimethylammonium bromide in a yield of 35%; mp 41-43 ° C; Rf = 0.54; IR spectral characteristics: 9 (CO) 1736, -Q (COC) 1177, -Q (CN) 1105 cm -1 (in nujol suspension).
Přiklad 2Example 2
Pracovný postup je ten istý ako v přiklade 1, do reakcie sa použil hexylester kyseliny 11-brómundekánovej. Vzniká N-dodecyl-(10-hexyloxykarbonyldecyl)dimetylamóniumbromid vo výtažku 41 %; t.t, 53 až 55 QC; Rp=0,50; IČ-spektrálne charakteristiky: 9 (CO) 1731,Á)(C0C) 1184, Ý(CN) 1119 cm“1 /v nujolovej suspenzi!/.The procedure is the same as in Example 1, except that 11-bromo-nanoic acid hexyl ester is used in the reaction. N-dodecyl (10-hexyloxycarbonyldecyl) dimethylammonium bromide is obtained in a yield of 41%; mp. 53 to 55 Q C; Rf = 0.50; IR spectral characteristics: 9 (CO) 1731,? (COC) 1184,? (CN) 1119 cm -1 (in nujol suspension).
Příklad 3Example 3
Pracovný postup je ten istý ako v příklade 1, do reakcie sa použil benzylester kyseliny 11-brómundekánovej. Vzniká N-dodecyl-(10-benzyloxykarbonyldecyl)dimetylamóniumbromid vo výtažku 45 RF=0,55; IČ-spektrálne charakteristiky: 0 (CO) 1735, 9(C0C) 1171, Á>(CN) 1116 cm”1 /v nujolovej suspenzi!/.The procedure was the same as in Example 1, but the reaction was treated with 11-bromo-decanoic acid benzyl ester. There is a N-dodecyl (10 benzyloxykarbonyldecyl) dimethyl ammonium bromide in a yield of 45 Rf = 0.55; IR spectral characteristics: 0 (CO) 1735, 9 (COC) 1171,? (CN) 1116 cm -1 (in a nujol suspension).
PREDMETVYNALÉZUPREDMETVYNALÉZU
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776478A CS200114B1 (en) | 1978-11-27 | 1978-11-27 | Ammonium salts of esters of 11-aminoundecanoic acid and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776478A CS200114B1 (en) | 1978-11-27 | 1978-11-27 | Ammonium salts of esters of 11-aminoundecanoic acid and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200114B1 true CS200114B1 (en) | 1980-08-29 |
Family
ID=5427326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776478A CS200114B1 (en) | 1978-11-27 | 1978-11-27 | Ammonium salts of esters of 11-aminoundecanoic acid and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200114B1 (en) |
-
1978
- 1978-11-27 CS CS776478A patent/CS200114B1/en unknown
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