DE530397C - Process for the preparation of o-aminooxyalkylaminobenzolar acids - Google Patents
Process for the preparation of o-aminooxyalkylaminobenzolar acidsInfo
- Publication number
- DE530397C DE530397C DEI35119D DEI0035119D DE530397C DE 530397 C DE530397 C DE 530397C DE I35119 D DEI35119 D DE I35119D DE I0035119 D DEI0035119 D DE I0035119D DE 530397 C DE530397 C DE 530397C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acids
- preparation
- amino
- aminooxyalkylaminobenzolar
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000007513 acids Chemical class 0.000 title description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 B. ethanolamine Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- VCHSXYHBMFKRBK-UHFFFAOYSA-N 4771-47-5 Chemical compound OC(=O)C1=CC=CC(Cl)=C1[N+]([O-])=O VCHSXYHBMFKRBK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical class O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von o-Aminooxyalkylaminobenzolarsinsäuren Durch Patent 412 I71 ist ein Verfahren zur Darstellung von Oxyalkylaminoarsinsäuren geschützt. Diese Verbindungen werden erhalten durch Umsetzung von Arsinsäuren, welche eine oder mehrere Aminogruppen im Molekül haben, mit Äthylenoxyd, dessen Homologen oder Derivaten.Process for the preparation of o-aminooxyalkylaminobenzolar acids By patent 412,171 is a method for the preparation of oxyalkylaminoarsinic acids protected. These compounds are obtained by reacting arsinic acids, which have one or more amino groups in the molecule, with ethylene oxide, its homologues or derivatives.
Es wurde nun gefunden, daß o-Aminooxyalkyl.aminobenzolarsi.n.säuren, zu welchen die sehr wertvolle 3-Amino-4-äth,anolaminobenzol-i-arsinsäure gehört, in einfachster Weise durch Umsetzung der o-Nitrochlorbenzolarsinsäure mit aliphatischen o)-Amino,alkoholen, z. B. Äthanolamin, und anschließende Reduktion der Nitrogruppe herzustellen sind.It has now been found that o-aminooxyalkyl.aminobenzolarsi.n.acids, to which the very valuable 3-amino-4-ether, anolaminobenzene-i-arsic acid belongs, in the simplest way by reacting o-nitrochlorobenzenic acid with aliphatic o) -amino, alcohols, e.g. B. ethanolamine, and subsequent reduction of the nitro group are to be produced.
Beispiel 420 g 3-Nitro-4-chlorbenzol-i-arsinsäure werden in 48o ccm Wasser und I24,5, ccm Natronlauge (40° Be) eingetragen, 276 g Äthanolamin zugegeben und auf dem Dampfbad 6 Stunden erwärmt. Aus der filtrierten :erkalteten Lösung scheidet Salzsäure die 3--Nitro-4räthanolaminobenzol- i-arsinsäure ab. 3o6 g der Säure werden in i Zoo ccm Wasser und 166 ccm Natronlauge (4o° Be) gelöst, die Lösung auf o° abgekühlt und unter lebhaftem Rühren 652, g Hydrosulfit zugegeben. Nachdem Entfärbung eingetreten ist, wird nach Zugabe von 2o g Tierkohle aufgekocht und filtriert. Zum Filtrat gibt man 2o4 ccm konzentrierte Salzsäure, worauf die 3'- Amino-4-äthanolaminobenzol- i -,arsinsäure auskristallisiert. Sie bildet ein wenig gefärbtes kristallines Pulver, löslich in Alkalien, Säuren und Wasser.Example 420 g of 3-nitro-4-chlorobenzene-i-arsic acid are dissolved in 48o ccm Water and I24.5 ccm of sodium hydroxide solution (40 ° Be) added, 276 g of ethanolamine added and heated on the steam bath for 6 hours. From the filtered: cooled solution separates Hydrochloric acid removes the 3 - nitro-4rathanolaminobenzol- i-arsinic acid. 3o6 g of the acid dissolved in 1 zoo cc of water and 166 cc of sodium hydroxide solution (40 ° Be), the solution cooled to 0 ° and 652 g hydrosulfite were added with vigorous stirring. After discoloration occurred is, after adding 20 g of animal charcoal, it is boiled and filtered. Add to the filtrate one 2o4 ccm of concentrated hydrochloric acid, whereupon the 3'-amino-4-ethanolaminobenzene i -, arsic acid crystallized out. It forms a little colored crystalline powder, soluble in alkalis, acids and water.
Die Säure zeichnet sich durch geringe Giftigkeit bei guter Wirkung ,aus. Die Dos. tol. ist '/" bei einer Dos. cur. von '300, der Index ist somit 1/20. Im Gegensatz zu dieser Verbindung zeigen die hydroxylfreien Alkylaminoderivate erheblich höhere Giftigkeit. So ist die 3-Amino-4-äthylaminobenzolaminsäure mindestens zehnmal so giftig wie die 3-Amino-4-äthanolaminabenzolarsinsäure gemäß vorliegender Erfindung. Dabei treten bei- Anwendung der halben Dos. tol. noch Rezidive auf. Dieselben Verhältnisse ergaben sich bei der Prüfung der homologen 3-Amino-4-propylaminosäure. Auch diese ist zehn- bis fünfzehnmal giftiger als das Oxyäthylaminderivat und zeigt dabei sehr schlechte Heilwirkung.The acid is characterized by low toxicity and good effects ,the end. The Dos. tol. is '/ "with a Dos. cur. of' 300, the index is therefore 1/20. In contrast to this compound, the hydroxyl-free alkylamino derivatives show significant higher toxicity. So is the 3-amino-4-ethylaminobenzolamic acid at least ten times as toxic as the 3-amino-4-ethanolaminabenzolaric acid according to the present invention. When doing this, apply half the dose. tol. still relapses. Same conditions found when testing the homologous 3-amino-4-propylamino acid. These too is ten to fifteen times more toxic than the oxyethylamine derivative and shows a lot bad healing properties.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35119D DE530397C (en) | 1928-08-02 | 1928-08-02 | Process for the preparation of o-aminooxyalkylaminobenzolar acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35119D DE530397C (en) | 1928-08-02 | 1928-08-02 | Process for the preparation of o-aminooxyalkylaminobenzolar acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE530397C true DE530397C (en) | 1931-07-29 |
Family
ID=7188896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI35119D Expired DE530397C (en) | 1928-08-02 | 1928-08-02 | Process for the preparation of o-aminooxyalkylaminobenzolar acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE530397C (en) |
-
1928
- 1928-08-02 DE DEI35119D patent/DE530397C/en not_active Expired
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