DE433105C - Process for the preparation of water-soluble derivatives by salt-forming atomic groups of substituted aryl arsenic acids, aryl stibic acids and the corresponding oxides - Google Patents
Process for the preparation of water-soluble derivatives by salt-forming atomic groups of substituted aryl arsenic acids, aryl stibic acids and the corresponding oxidesInfo
- Publication number
- DE433105C DE433105C DEF56338D DEF0056338D DE433105C DE 433105 C DE433105 C DE 433105C DE F56338 D DEF56338 D DE F56338D DE F0056338 D DEF0056338 D DE F0056338D DE 433105 C DE433105 C DE 433105C
- Authority
- DE
- Germany
- Prior art keywords
- acids
- water
- aryl
- preparation
- salt
- 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 7
- 150000007513 acids Chemical class 0.000 title claims description 4
- 125000003118 aryl group Chemical group 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 7
- 238000000034 method Methods 0.000 title description 3
- -1 substituted aryl arsenic acids Chemical class 0.000 title description 2
- 208000007976 Ketosis Diseases 0.000 claims description 3
- 150000001323 aldoses Chemical class 0.000 claims description 3
- 150000002584 ketoses Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- MWZAMPYHMUSARJ-UHFFFAOYSA-M stibinic acid Chemical class O[SbH2]=O MWZAMPYHMUSARJ-UHFFFAOYSA-M 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- HIRHVIKSACPKMV-UHFFFAOYSA-N [H][Sb]([H])C1=CC(N)=CC=C1.Cl Chemical compound [H][Sb]([H])C1=CC(N)=CC=C1.Cl HIRHVIKSACPKMV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- XQPGASWSZLFUSJ-UHFFFAOYSA-N NC=1C=C(C=CC=1)[SbH2]=O Chemical compound NC=1C=C(C=CC=1)[SbH2]=O XQPGASWSZLFUSJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- XKNKHVGWJDPIRJ-UHFFFAOYSA-N arsanilic acid Chemical compound NC1=CC=C([As](O)(O)=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-N 0.000 description 1
- 229950002705 arsanilic acid Drugs 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001556 precipitation Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von wasserlöslichen Derivaten durch salzbildende Atomgruppen substituierter Arylarsinsäuren, Arylstibinsäuren und der entsprechenden Oxyde. Durch das Hauptpatent 413147 ist ein Verfahren zur Darstellung von wasserlöslichen Derivaten durch salzbildende Atomgruppen substituierter Arylarsine geschützt, darin bestehend, claß man auf diese Verbindungen Aldosen oder Ketosen einwirken läßt.Process for the preparation of water-soluble derivatives by salt-forming Atomic groups of substituted arylarsinic acids, arylstibinic acids and the corresponding Oxides. The main patent 413147 describes a process for the preparation of water-soluble Derivatives protected by salt-forming atomic groups of substituted aryl arsines, therein consisting of allowing aldoses or ketoses to act on these compounds.
Es wurde nun weiterhin gefunden, daß durch Einwirkung von Aldosen oder Ketosen auf Amino- oder Aminooxyarylarsin- oder -stibinsäuren oder die entsprechenden Oxyde ebenfalls wasserlösliche Derivate erhalten werden, die aus den entstandenen wässerigen Lösungen durch Fällungsmittel organischer Natur in fester Form abgeschieden werden können.It has now also been found that by the action of aldoses or ketoses on amino or aminooxyarylarsinic or stibinic acids or the corresponding Oxides can also be obtained from the resulting water-soluble derivatives aqueous solutions deposited in solid form by precipitants of an organic nature can be.
Beispiele. r. 11,5 g salzsaures 3 Arnino-.f-oxybenzolarsinoxyd werden in 70 ccm 5oprozentige Glucoselösung eingetragen, 4.,2 cctn Natronlauge von d.0° B8 zugesetzt und unter Luftabschluß bei 6o° gerührt, bis eine gezogene Probe in Wasser klar löslich und nicht mehr diazotierbar ist. Die erkaltete Lösung wird mit Salzsäure neutralisiert, filtriert und in 1,75 1 Alkohol eingerührt. Nachdem noch 875 ccm Äther zugegeben wurden, wird die ausgeschiedene weiße Verbindung abgetrennt und im Vakuum getrocknet. Sie ist klar löslich in Wasser.Examples. r. 11.5 g hydrochloric acid 3 arnino-.f-oxybenzolar oxide are introduced into 70 cc of 5% glucose solution, 4 can no longer be diazotized. The cooled solution is neutralized with hydrochloric acid, filtered and stirred into 1.75 liters of alcohol. After a further 875 ccm of ether have been added, the precipitated white compound is separated off and dried in vacuo. It is clearly soluble in water.
2. m-Aminophenylstibinsäure, gewonnen aus 6 g salzsaurem m-Aminophenylstibinchlorür, gut abgesaugt und gewaschen, werden in 2o ccm Wasser angerührt, mittels 1,66 ccm Natronlauge (d.o° Be) in Lösung gebracht und nach Zugabe von ro g Galactose im Wasserbad bei 5o° 5 Stunden gerührt. Nachdem mit Essigsäure schwach angesäuert wurde, wird filtriert und das Präparat durch Einrühren in 25 Teile Alkohol gefällt. Es ist 1;lar löslich in Wasser.2. m-aminophenylstibic acid, obtained from 6 g of hydrochloric acid m-aminophenylstibin chloride, well sucked off and washed, are mixed in 2o ccm of water, using 1.66 ccm Sodium hydroxide solution (d.o ° Be) brought into solution and after adding ro g galactose in a water bath stirred at 5o ° for 5 hours. After being weakly acidified with acetic acid, becomes filtered and the preparation precipitated by stirring into 25 parts of alcohol. It is 1; lar soluble in water.
3. 2o g m-N itrophenylstibinsäure werden zum m-Aminophenylstibinchlorür reduziert und dieses durch Verreiben mit Eis und Zugabe von Ammoniak in das m-Aminophenylstibinoxyd übergeführt. Von diesem wird abgesaugt, ausgewaschen und das gut abgesaugte Produkt in 48 ccm Wasser angerührt, 36 g Lactose zugegeben und im Wasserbad bei 5o° 5112 Stunden gerührt. Dann wird filtriert und die Lösung in 25 Teile Alkohol eingerührt. Von der Fällung wird abgesaugt, mit Alkohol undÄther gewaschen und imVakuum getrocknet. Das Präparat ist wasserlöslich.3. 20 g of m-nitrophenylstibic acid become m-aminophenylstibine chloride reduced and this by rubbing with ice and adding ammonia to the m-aminophenylstibinoxide convicted. This is sucked off, washed out and the well sucked off product Stirred in 48 cc of water, 36 g of lactose added and in a water bath at 50 ° 5112 Stirred for hours. It is then filtered and the solution is stirred into 25 parts of alcohol. The precipitation is suctioned off, with Alcohol and ether washed and dried in vacuum. The preparation is soluble in water.
11,5 g 3-Amino-4-oxybenzol-l-arsinsäure werden in 55 ccm Wasser und 4,2 cctn Natronlauge (40° Be) gelöst, 27 g Glucose zugegeben und im Wasserbad bei 55° 6'/, Stunden gerührt. Die Aufarbeitung der Lösung erfolgt, wie in Beispiel 2 angegeben. Das Präparat ist klar löslich in Wasser.11.5 g of 3-amino-4-oxybenzene-l-arsic acid are dissolved in 55 cc of water and 4.2 cc of sodium hydroxide solution (40 ° Be), 27 g of glucose are added and the mixture is stirred in a water bath at 55 ° for 6 1/2 hours. The solution is worked up as indicated in Example 2. The preparation is clearly soluble in water.
5. 1o,5 g Arsanilsäure werden in 45 ccjn Wasser und 4,2 ccin NaOH (4o° Be) gelöst und nach Zusatz von 22,5 g Arabinose itn Wasserbad bei 55° 6'1_ Stunden gerührt. Die Lösung wird, wie in Beispiel e angegeben, aufgearbeitet. Das so erhaltene Präparat ist wasserlöslich.5. 10.5 g of arsanilic acid are dissolved in 45 cc of water and 4.2 cc of NaOH (40 ° Be) and after adding 22.5 g of arabinose in a water bath at 55 ° 6'1_ Stirred for hours. The solution is worked up as indicated in example e. That The preparation obtained in this way is soluble in water.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF56338D DE433105C (en) | 1924-06-24 | 1924-06-24 | Process for the preparation of water-soluble derivatives by salt-forming atomic groups of substituted aryl arsenic acids, aryl stibic acids and the corresponding oxides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF56338D DE433105C (en) | 1924-06-24 | 1924-06-24 | Process for the preparation of water-soluble derivatives by salt-forming atomic groups of substituted aryl arsenic acids, aryl stibic acids and the corresponding oxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE433105C true DE433105C (en) | 1926-08-20 |
Family
ID=7107939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF56338D Expired DE433105C (en) | 1924-06-24 | 1924-06-24 | Process for the preparation of water-soluble derivatives by salt-forming atomic groups of substituted aryl arsenic acids, aryl stibic acids and the corresponding oxides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE433105C (en) |
-
1924
- 1924-06-24 DE DEF56338D patent/DE433105C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1643320C3 (en) | Process for the production of pentachlorothiophenol | |
| DE3615348A1 (en) | METHOD FOR PRODUCING BASIC ZINC CARBONATE | |
| DE433105C (en) | Process for the preparation of water-soluble derivatives by salt-forming atomic groups of substituted aryl arsenic acids, aryl stibic acids and the corresponding oxides | |
| DE1154119B (en) | Process for the preparation of 2- (2 ', 4', 6'-trimethylbenzyl) -1, 3-diazacyclopentene- (2) and its salts | |
| DE681523C (en) | Process for the preparation of quaternary ammonium compounds | |
| DE423036C (en) | Process for the preparation of derivatives of aromatic arsenic compounds and their metal complex compounds | |
| DE413147C (en) | Process for the preparation of water-soluble derivatives of aryl arsines substituted by salt-forming atom groups | |
| DE660578C (en) | Process for the extraction of gold compounds from water-soluble keratin breakdown products | |
| DE828105C (en) | Process for the production of bactericidal oil-soluble substances | |
| DE565065C (en) | Process for the separate recovery of a hypertensive substance and a uterine muscle contracting substance from the posterior lobe of the pituitary gland | |
| DE719026C (en) | Process for the production of preparations containing the circulatory hormone kallikrein | |
| DE412171C (en) | Process for the preparation of organic arsenic and antimony compounds which are soluble in water | |
| DE487105C (en) | Process for the preparation of monoacyl derivatives of cyclic aminothiophenol carbon and sulfonic acids | |
| DE445669C (en) | Process for the preparation of organic compounds with trivalent arsenic | |
| DE268451C (en) | ||
| DE720937C (en) | Process for the production of therapeutically valuable gold compounds from keratin breakdown products | |
| DE945236C (en) | Process for the production of water-soluble bismuth compounds of ª ‡ -oxy-ª ‡ -phosphono-propionic acid | |
| DE568943C (en) | Process for the representation of asymmetrical arsenic compounds | |
| DE623450C (en) | ||
| AT150297B (en) | Process for the preparation of unsymmetrical aromatic arsenic compounds. | |
| DE837694C (en) | Process for the preparation of a new condensation product of 2- (4-aminobenzene-1'-sulfonamido) -thiazole | |
| DE488574C (en) | Process for the preparation of asymmetrical heterocyclic arsenic compounds | |
| DE215007C (en) | ||
| DE728069C (en) | Process for the production of therapeutically valuable gold compounds from keratin breakdown products | |
| DE703103C (en) | indications from keratin breakdown products |