DE1222930B - Process for the production of new tin complex salts - Google Patents
Process for the production of new tin complex saltsInfo
- Publication number
- DE1222930B DE1222930B DEB74613A DEB0074613A DE1222930B DE 1222930 B DE1222930 B DE 1222930B DE B74613 A DEB74613 A DE B74613A DE B0074613 A DEB0074613 A DE B0074613A DE 1222930 B DE1222930 B DE 1222930B
- Authority
- DE
- Germany
- Prior art keywords
- formula
- nitrogen atom
- radicals
- saturated
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- -1 araliphatic Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 2
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical class C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2204—Not belonging to the groups C07F7/2208 - C07F7/2296
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von neuen Zinnkomplexsalzen Zusatz zur Anmeldung: B 71289 IV d/12 p -Auslegeschrift 1 219 029 Gegenstand der Patentanmeldung B 71 289 IVdI12p (deutsche Auslegeschrift 1 219 029) ist ein Verfahren zur Herstellung von neuen Zinnkomplexsalzen der Formel in der Bindungen am Stickstoffatom durch Ru bis R4 abgesättigt sind, wobei R1 bis R4, die gleich oder verschieden sein können, Wasserstoffatome, gegebenenfalls substituierte aliphatische, alicyclische, araliphatische oder aromatische Kohlenwasserstoffreste, zwei der Reste R1 bis R4 zusammen mit dem Stickstoffatom des Kations einen gegebenenfalls substituierten gesättigten oder teilweise gesättigten heterocyclischen Ring, drei der Reste R1 bis R4 zusammen mit dem Stickstoffatom einen gegebenenfalls substituierten ungesättigten heterocyclischen Ring bedeuten können und wobei R1 bis R4 nicht ausschließlich Wasserstoff bedeuten können und X und Y, die gleich oder verschieden sein können, Anionen anorganischer oder organischer Säuren, vorzugsweise Anionen einer Halogenwasserstoffsäure oder einer organischen Sulfonsäure, bedeuten, das dadurch gekennzeichnet ist, daß man ein Ammoniumsalz der Formel in der R1 bis R4 und X die oben angeführte Bedeutung haben, mit einem Triphenylzinnsalz der Formel (C8H5)3 SnY III in der Y die angeführte Bedeutung aufweist, umsetzt.Process for the production of new tin complex salts in the bonds on the nitrogen atom are saturated by Ru to R4, where R1 to R4, which can be identical or different, are hydrogen atoms, optionally substituted aliphatic, alicyclic, araliphatic or aromatic hydrocarbon radicals, two of the radicals R1 to R4 together with the nitrogen atom of the cation optionally substituted saturated or partially saturated heterocyclic ring, three of the radicals R1 to R4 together with the nitrogen atom can represent an optionally substituted unsaturated heterocyclic ring and where R1 to R4 cannot exclusively represent hydrogen and X and Y, which can be identical or different, are anions inorganic or organic acids, preferably anions of a hydrohalic acid or an organic sulfonic acid, which is characterized in that an ammonium salt of the formula in which R1 to R4 and X have the meaning given above, is reacted with a triphenyltin salt of the formula (C8H5) 3 SnY III in which Y has the meaning given.
Die neuen Verbindungen besitzen eine gute antimikrobielle, besonders bakterizide und fungizide Wirksamkeit und wirken außerdem molluskizid. The new compounds have good antimicrobial properties, especially bactericidal and fungicidal effectiveness and also have a molluscicidal effect.
Es wurde nun gefunden, daß sich Verbindungen der Formel I, in denen X und Y Halogenatome bedeuten, besonders einfach dadurch herstellen lassen, daß man ein tertiäres Amin der Formel in der R1 bis R3 die oben angeführte Bedeutung haben, gleichzeitig mit einer Verbindung der Formel R4X V in der R4 die oben angeführte Bedeutung mit Ausnahme eines Wasserstoffatoms oder eines Arylrestes hat und X für ein Halogenatom steht, und mit einem Triphenylzinnsalz der Formel (CßH6)3 SnY III in der Y ein Halogenatom bedeutet, bei erhöhten Temperaturen, vorzugsweise zwischen 80 und 150"C, und gegebenenfalls im geschlossenen Gefäß umsetzt.It has now been found that compounds of the formula I in which X and Y denote halogen atoms can be prepared particularly easily by using a tertiary amine of the formula in which R1 to R3 have the meaning given above, simultaneously with a compound of the formula R4X V in which R4 has the meaning given above with the exception of a hydrogen atom or an aryl radical and X stands for a halogen atom, and with a triphenyltin salt of the formula (CßH6) 3 SnY III in which Y is a halogen atom, is reacted at elevated temperatures, preferably between 80 and 150 ° C., and optionally in a closed vessel.
Die Umsetzung erfolgt zweckmäßig unter Anwendung äquivalenter Mengen der Ausgangsstoffe bei erhöhten Temperaturen, vorzugsweise bei Temperaturen zwischen 80 und 1500 C, in einem inerten Lösungsmittel. The reaction is expediently carried out using equivalent amounts the starting materials at elevated temperatures, preferably at temperatures between 80 and 1500 C, in an inert solvent.
Falls die eingesetzten Verbindungen der Formel IV und V oder das verwendete Lösungsmittel einen niedrigen Siedepunkt haben, wird zweckmäßig im geschlossenen Gefäß gearbeitet. Als Lösungsmittel könnenbeispielsweise Methylenchlorid,Äthylenchlorid, Methanol, Äthanol, Chloroform, Dioxan, Dimethylformamid, Acetonitril und Aceton verwendet werden.If the compounds of the formulas IV and V used or the one used Solvents have a low boiling point, is expedient in the closed Vessel worked. As a solvent, for example, methylene chloride, ethylene chloride, Methanol, ethanol, chloroform, dioxane, dimethylformamide, acetonitrile and acetone be used.
Die Aufarbeitung erfolgt auf die übliche Weise entweder durch Ausfällen des Komplexsalzes mit Äther oder durch Abdampfen des Lösungsmittels. In beiden Fällen wird das Rohprodukt durch Umkristallisation gereinigt.Working up is carried out in the usual way either by precipitation of the complex salt with ether or by evaporation of the solvent. In both cases the crude product is purified by recrystallization.
Das vorliegende Verfahren stellt eine wesentliche Vereinfachung gegenüber dem Verfahren des Hauptpatents dar, da die langwierige Herstellung und Isolierung der quaternären Ammoniumsalze wegfällt und die Endprodukte in einem einzigen Reaktionsgang erhalten werden. The present procedure contrasts with a substantial simplification the process of the main patent because of the tedious production and isolation of the quaternary ammonium salts and the end products in a single reaction can be obtained.
Die folgenden Beispiele dienen zur Erläuterung der Erfindung: Beispiel 1 7,9 g (0,1 Mol) Pyridin, 13,7 g (0,1 Mol) Butylbromid und 38 g (0,1 Mol) Triphenylzinnchiorid werden in 200 ml Methanol gelöst und im Bombenrohr 8 Stunden auf 100"C erhitzt. Dann wird das Lösungsmittel abgedampft und der Rückstand aus Isopropanol umkristallisiert. Man erhält 50 g (83°/o der Theorie Ausbeute) N-Butylpyridinium-triphenylbrom-chlor-stannat vom F. = 113 bis 115"C. The following examples serve to illustrate the invention: Example 1 7.9 g (0.1 mole) pyridine, 13.7 g (0.1 mole) butyl bromide and 38 g (0.1 mole) triphenyltin chloride are dissolved in 200 ml of methanol and heated to 100 ° C. for 8 hours in a sealed tube. The solvent is then evaporated off and the residue is recrystallized from isopropanol. 50 g (83% of theoretical yield) of N-butylpyridinium triphenylbromochlorostannate are obtained from F. = 113 to 115 "C.
Beispiel 2 10,1 g (0,1 Mol) Triäthylamin, 10,9 g (0,1 Mol) Äthylbromid und 38,5 g Triphenylzinnchlorid werden wie oben zur Reaktion gebracht; die Lösung wird dann mit Äther versetzt und das ausgeschiedene Tetraäthylamrnonium-triphenyl-brom-chlor-stannat aus Isopropanol umkristallisiert. Die Ausbeute beträgt 46,5 g (78 0/o der Theorie). Die Substanz hat den F. = 134 bis 135"C. Example 2 10.1 g (0.1 mol) of triethylamine, 10.9 g (0.1 mol) of ethyl bromide and 38.5 g of triphenyltin chloride are reacted as above; the solution ether is then added and the precipitated tetraethylammonium triphenyl bromochlorostannate recrystallized from isopropanol. The yield is 46.5 g (78% of theory). The substance has the F. = 134 to 135 "C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB74613A DE1222930B (en) | 1963-12-10 | 1963-12-10 | Process for the production of new tin complex salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB74613A DE1222930B (en) | 1963-12-10 | 1963-12-10 | Process for the production of new tin complex salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1222930B true DE1222930B (en) | 1966-08-18 |
Family
ID=6978324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB74613A Pending DE1222930B (en) | 1963-12-10 | 1963-12-10 | Process for the production of new tin complex salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1222930B (en) |
-
1963
- 1963-12-10 DE DEB74613A patent/DE1222930B/en active Pending
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