DE206344C - - Google Patents
Info
- Publication number
- DE206344C DE206344C DENDAT206344D DE206344DA DE206344C DE 206344 C DE206344 C DE 206344C DE NDAT206344 D DENDAT206344 D DE NDAT206344D DE 206344D A DE206344D A DE 206344DA DE 206344 C DE206344 C DE 206344C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitrophenylarsinic
- solution
- treated
- aminophenylarsinic
- 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
- 239000000243 solution Substances 0.000 claims description 6
- XRRYKLCARXYQBX-UHFFFAOYSA-N NC=1C=C(C=CC=1)[AsH](O)=O Chemical compound NC=1C=C(C=CC=1)[AsH](O)=O XRRYKLCARXYQBX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims description 4
- 229910001023 sodium amalgam Inorganic materials 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- -1 phenylarsinic acid nitrophenylarsinic acid Chemical compound 0.000 claims description 2
- WRRQKFXVKRQPDB-UHFFFAOYSA-N 2-(2-aminophenyl)sulfanylaniline Chemical class NC1=CC=CC=C1SC1=CC=CC=C1N WRRQKFXVKRQPDB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CABPOUXEDUPRCE-UHFFFAOYSA-N nitro(phenyl)arsinic acid Chemical compound O[As](=O)(C1=CC=CC=C1)[N+]([O-])=O CABPOUXEDUPRCE-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006477 desulfuration reaction Methods 0.000 description 2
- 230000023556 desulfurization Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical group O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XLNJLYSLXXLENR-UHFFFAOYSA-N N[As]C1=CC=CC=C1 Chemical compound N[As]C1=CC=CC=C1 XLNJLYSLXXLENR-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical compound [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- YKQNYRADBBHWOK-UHFFFAOYSA-N phenylarsonamidic acid Chemical compound N[As](O)(=O)C1=CC=CC=C1 YKQNYRADBBHWOK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 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
bmqiifrügv" bez. tstnivi-n.Mi.-nqbmqiifrügv "re . tstnivi-n.Mi.-nq
Gj-utppcGj-utppc
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Reduktion der von Michaelis (B. 27 [1894], S. 265; A. 320 [1902], S. 294) dargestellten Nitrophenylarsinsäure, die den Substitutionsgesetzen zufolge die Nitrogruppe zum Arsensäurerest in Metastellung enthalten muß, zur entsprechenden m - Aminophenylarsinsäure ist bisher nicht gelungen (s. A. 320 [1902], S. 277). Nur ein Aminophenylarsensulfid, N H2CeHiAs S, wurde von Michaelis (Ber. 27 [1894], S. 271) dargestellt.The reduction of the nitrophenylarsinic acid presented by Michaelis (B. 27 [1894], p. 265; A. 320 [1902], p. 294), which according to the laws of substitution must contain the nitro group meta to the arsenic acid residue, to the corresponding m-aminophenylarsinic acid not yet successful (see A. 320 [1902], p. 277). Only one aminophenyl arsenic sulfide, NH 2 C e H i As S, was presented by Michaelis (Ber. 27 [1894], p. 271).
Es wurde nun gefunden, daß die m-Aminophenylarsinsäure (Metarsanilsäure) dargestellt werden kann:It has now been found that m-aminophenylarsinic acid (Metarsanilic acid) can be represented:
1. durch Einwirkung von Natriumamalgam auf jene bekannte Nitrophenylarsinsäure in alkoholischer Lösung,1. by the action of sodium amalgam on that known nitrophenylarsinic acid in alcoholic solution,
2. durch Entschwefelung der bei der Einwirkung von Schwefelammonium auf Nitrophenylarsinsäure entstehenden Aminophenylarsensulfide mit Metalloxyden in alkalischer Lösung.2. by desulfurization of the action of ammonium sulphide on nitrophenylarsinic acid resulting aminophenyl arsenic sulfides with metal oxides in alkaline Solution.
Da bei der Darstellung dieser Sulfide ein Gemenge verschiedener Oxydationsstufen:Since in the representation of these sulphides a mixture of different oxidation stages:
v.v.
III.III.
und NH2C6HiAsS and NH 2 C 6 HiAsS
erhalten wird, so empfiehlt es sich, zur Entschwefelung Kupferoxyd anzuwenden, wobei die Derivate des dreiwertigen Arsens zugleich wieder oxydiert werden.is obtained, it is advisable to use copper oxide for desulfurization, with the derivatives of trivalent arsenic are oxidized again at the same time.
I. Reduktion der Nitrophenylarsinsäure mit Natriumamalgam.I. Reduction of nitrophenylarsinic acid with sodium amalgam.
99 g Nitrophenylarsinsäure werden in 21 Methylalkohol gelöst und mit 2,8 kg 4prozentigem Natriumamalgam so lange bei 500 digeriert, bis die Wasserstoffentwicklung aufgehört hat. Hierauf wird vom Quecksilber abfiltriert, der Methylalkohol abdestilliert, der Rückstand mit 8 bis 9 1 Wasser aufgenommen und die Lösung mit Essigsäure neutralisiert. Auf Zusatz von überschüssigem Zinkacetat fällt das Zinksalz der m - Aminophenylarsinsäure aus, das mit Natriumcarbonat zerlegt wird. Das Filtrat von Zinkcarbonat, mit Salzsäure neutralisiert, scheidet auf Zusatz von Eisessig die Metarsanilsäure als weißes Pulver ab.99 g are dissolved in 21 Nitrophenylarsinsäure methyl alcohol and digested with 2.8 kg 4prozentigem sodium amalgam as long as at 50 0, stopped until the evolution of hydrogen. The mercury is then filtered off, the methyl alcohol is distilled off, the residue is taken up in 8 to 9 liters of water and the solution is neutralized with acetic acid. When excess zinc acetate is added, the zinc salt of m-aminophenylarsinic acid precipitates and is broken down with sodium carbonate. The filtrate of zinc carbonate, neutralized with hydrochloric acid, separates the metarsanilic acid as a white powder when glacial acetic acid is added.
II. Reduktion mit Schwefelammonium. _0 II. Reduction with sulfur ammonium. _ 0
200 g Nitrophenylarsinsäure werden in 1,4 1 25 prozentigem Ammoniaks gelöst, die Lösung mit Schwefelwasserstoff gesättigt, darauf 12 Stunden auf dem Wasserbade erwärmt und die Behandlung mit Schwefelwasserstoff und das Erwärmen nochmals wiederholt. Hierauf wird zur Trockne gedampft,- der Rückstand mehrfach mit stark verdünnter Salzsäure ausgezogen, die Auszüge auf 10 1 verdünnt und nach Zufügung von 1,41 zehnfach normaler200 g of nitrophenylarsinic acid are dissolved in 1.4 liters of 25 percent ammonia, the solution saturated with hydrogen sulfide, then warmed on the water bath for 12 hours and the treatment with hydrogen sulfide and the heating are repeated again. On that is evaporated to dryness, - the residue is extracted several times with very dilute hydrochloric acid, the extracts diluted to 10 1 and ten times more normal after the addition of 1.41
Natronlauge zum Sieden erhitzt. Man läßt nun so lange normale Kupfersulfatlösung zutropfen, bis eine filtrierte Probe beim Kochen mit Bleiacetat keinen Niederschlag von Schwefelblei mehr gibt. Man filtriert dann vom Schwefelkupfer ab, neutralisiert mit Essigsäure und gewinnt die freie Säure über das Zinksalz, wie im Beispiel I beschrieben.Sodium hydroxide solution heated to the boil. Normal copper sulphate solution is now allowed to drip in until until a filtered sample boiled with lead acetate no precipitate of lead sulfur more there. The copper sulphide is then filtered off and neutralized with acetic acid and wins the free acid via the zinc salt, as described in Example I.
Die m - Aminophenylarsinsäure (Metarsanilsäure) schmilzt bei 212 bis 2140, wodurch sie sich von der bei 2300 noch nicht schmelzenden ρ - Aminophenylarsinsäure unterscheidet. Sie kristallisiert aus Wasser in farblosen Prismen, ist schwer löslich in heißem Wasser, mäßig löslich in Methylalkohol, schwer löslich in Äthylalkohol, Eisessig und Äther. Von Alkalien und Mineralsäuren wird sie gelöst. Sie läßt sich leicht diazotieren und liefert mit Magnesiamischung erhitzt einen weißen Niederschlag.The m - Aminophenylarsinsäure (Metarsanilsäure) melts at 212-214 0, which extend from the not yet melting at 230 0 ρ - differs Aminophenylarsinsäure. It crystallizes from water in colorless prisms, is sparingly soluble in hot water, moderately soluble in methyl alcohol, sparingly soluble in ethyl alcohol, glacial acetic acid and ether. It is dissolved by alkalis and mineral acids. It can be easily diazotized and, when heated with a magnesia mixture, gives a white precipitate.
Die neue Verbindung dient therapeutischen Zwecken.The new compound is used for therapeutic purposes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE206344C true DE206344C (en) | 1900-01-01 |
Family
ID=468517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT206344D Expired DE206344C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE206344C (en) |
-
0
- DE DENDAT206344D patent/DE206344C/de not_active Expired
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