DE510449C - Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivatives - Google Patents
Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivativesInfo
- Publication number
- DE510449C DE510449C DEI31344D DEI0031344D DE510449C DE 510449 C DE510449 C DE 510449C DE I31344 D DEI31344 D DE I31344D DE I0031344 D DEI0031344 D DE I0031344D DE 510449 C DE510449 C DE 510449C
- Authority
- DE
- Germany
- Prior art keywords
- oxybenzylamine
- acid
- acyl derivatives
- preparation
- arsinic
- 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 15
- 125000002252 acyl group Chemical group 0.000 title claims description 6
- 150000007513 acids Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- RULWBFLPUAFFGY-UHFFFAOYSA-N 2-(hydroxymethyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1CO RULWBFLPUAFFGY-UHFFFAOYSA-N 0.000 description 2
- QGGFJIALGORYME-UHFFFAOYSA-N 4-(hydroxymethyl)isoindole-1,3-dione Chemical compound OCC1=CC=CC2=C1C(=O)NC2=O QGGFJIALGORYME-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010792 warming 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 6-Oxybenzylamin-3-arsinsäuren und deren Acylderivaten Es wurde gefunden, daß die im Patent 50; 638 beschriebene 6-Oxybenzylamin-3-arsinsäure und deren Acylderivate sich auch gewinnen lassen, indem man 4-Oxybenzol-iarsinsäure und deren Derivate mit Met4ylolbenzamid oder Methylolphthalimid in saurer Lösung kondensiert und die so erhaltenen Acylderivate gegebenenfalls verseift. Die so gewonnenen Verbindungen sind identisch mit den nach denn Verfahren des genannten Patents erhaltenen.Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their Acyl Derivatives It has been found that the compounds disclosed in Patent 50; 6-oxybenzylamine-3-arsic acid described in 638 and their acyl derivatives can also be obtained by adding 4-oxybenzene-iarsinic acid and their derivatives with methylolbenzamide or methylolphthalimide in acidic solution condensed and the acyl derivatives obtained in this way, optionally saponified. The ones won in this way Compounds are identical to those obtained by the method of the cited patent.
Beispiel i Eine Mischung von 22 kg 4-Oxybenzol-iarsinsäure (Natriumsalz) und 15 kg Methylolbenzamid wird unter Wasserkühlung in 6ookg Schwefelsäure von 66° Be bei 5 bis i5° eingerührt. Die so erhaltene Lösung wird nach i2stündigem Stehen in Eiswasser eingetragen und nach dem Abstumpfen der Mineralsäure mittels N atriumcarbonat mit Natriumchlorid gefällt. Die abgeschiedene Säure wird zur Reinigung aus Methylalkohol umkristallisiert. Sie ist identisch mit der nach Beispiel i des obenerwähnten Patents erhaltenen 6-Oxybenzoylbenzylamin-3-arsinsäure und läßt sich durch Erwärmen mit verdünnter Natronlauge leicht in die Oxybenzylaminarsinsäure des Beispiels 2 des genannten Patents überführen. Beispie12 Eine Mischung von 300 kg 4-Oxybenzol-iarsinsäure (Natriumsalz) und 18 o kg Methylolphthalimid wird unter Kühlung in 6oo kg Schwefelsäure von 66° B6 eingetragen, wobei man die Temperatur unterhalb 30° hält. Nach ungefähr z2 Stunden wird das Kondensationsprodukt durch Eintragen der Reaktionsmasse in Eiswasser abgeschieden. Der Niederschlag wird filtriert, mit Wasser gewaschen und durch Lösen in Natriumacetatlösung und Wiederausfällen mit Wasser gereinigt. Die so erhaltene 6-Oxy-N-phthaloylbenzylamin-3-arsinsäure ist identisch mit der in Beispiel 3 des obenerwähnten Patents beschriebenen Verbindung und läßt sich leicht in die Oxvbenzylatn.inars.insättre des Beispiels 2 jenes Patents überführen.Example I A mixture of 22 kg of 4-oxybenzene-iarsinsäure (sodium salt) and 1 5 kg Methylolbenzamid is stirred under cooling with water in 6ookg sulfuric acid by 66 ° Be at 5 to i5 °. The solution obtained in this way is added to ice water after standing for 12 hours and, after the mineral acid has been blunted, precipitated with sodium chloride using sodium carbonate. The separated acid is recrystallized from methyl alcohol for purification. It is identical to the 6-oxybenzoylbenzylamine-3-arsinic acid obtained according to Example i of the above-mentioned patent and can easily be converted into the oxybenzylaminarsinic acid of Example 2 of the above-mentioned patent by heating with dilute sodium hydroxide solution. Beispie12 A mixture of 300 kg of 4-oxybenzene-iarsinsäure (sodium salt) and 1 o 8 kg methylolphthalimide is added under cooling in 6oo kg of sulfuric acid of 66 ° B6, keeping the temperature below 30 °. After about two hours, the condensation product is deposited by pouring the reaction mass into ice water. The precipitate is filtered, washed with water and purified by dissolving in sodium acetate solution and reprecipitation with water. The 6-oxy-N-phthaloylbenzylamine-3-arsinic acid thus obtained is identical to the compound described in Example 3 of the above-mentioned patent and can easily be converted into the Oxvbenzylatn.inars.insättre of Example 2 of that patent.
Beispiel 3 Eine Mischung von 32o kg 3-Chlor-4-oxybenzol-i-arsinsäure (Natriumsalz) und i8okg l##I:ethylolphthalimid wird unter Kühlung in 6oo kg Schwefelsäure von 66° Be bei 2o bis 25° eingerührt. Nach 24 Stunden gießt man die Masse auf Eiswasser. Der so gebildete weiße kristallinische Niederschlag wird filtriert, mit Wasser neutral gewaschen und in der berechneten Menge kalter Natriumcarbonatlösung gelöst. Die Lösung wird filtriert und,durcl% Ansäuern die 5-Chlor-6-oxybenzylphthalimi!d-3-arsinsäure abgeschieden. Sie kristallisiert aus kochendem verdünntem Alkohol in kleinen Nadeln vom Schmelzpunkt 263 bis 264° und ist löslich in verdünnten Alkalien, in verdünnter Natriumcarbonat- und Acetatlösung, schwer löslich in heißem Alkohol, unlöslich in Äther, Benzol, Benzin und verdünnten Säuren.Example 3 A mixture of 320 kg of 3-chloro-4-oxybenzene-i-arsic acid (Sodium salt) and i8okg l ## I: ethylolphthalimide is cooled in 600 kg of sulfuric acid stirred in from 66 ° Be at 2o to 25 °. After 24 hours, the mass is poured onto ice water. The white crystalline precipitate thus formed is filtered, neutralized with water washed and in the calculated amount of cold sodium carbonate solution solved. The solution is filtered and the 5-chloro-6-oxybenzylphthalimido-3-arsic acid is acidified deposited. It crystallizes in small needles from dilute boiling alcohol from melting point 263 to 264 ° and is soluble in dilute alkalis, in dilute Sodium carbonate and acetate solution, sparingly soluble in hot alcohol, insoluble in Ether, benzene, gasoline and diluted acids.
Durch Erwärmen mit verdünnter Natronlauge läßt sie sich leicht in die 5-Chlor-6-oxybenzylamin-3-arsinsäure überführen. Diese Verbindung zersetzt sich bei 22o°, ist unlöslich in Äther, Benzol und Ligroin, schwer löslich in Wasser und heißem Alkohol, löslich in verdünnter Salzsäure, Natriumcarbonat-, Natriumhydroxyd- und heißer Acetatlösung. B eisp,iel q.By warming it up with dilute caustic soda it can easily be in convert the 5-chloro-6-oxybenzylamine-3-arsic acid. This connection breaks down at 22o °, is insoluble in ether, benzene and ligroin, sparingly soluble in water and hot alcohol, soluble in dilute hydrochloric acid, sodium carbonate, sodium hydroxide and hot acetate solution. Example q.
Ersetzt man in Beispiel 3 die 3-Chlor-.4-oxybenzol-i-arsinsäure durch die entsprechende Menge 3-Methyl-q.-oxy'benzol-i-arsinsäure und arbeitet im übrigen in gleicher Weise, so erhält man 5-Methyl-6-oxybenzylphthalimid-3-arsinsäure, die bereits in Beispiel q. des obenerwähnten Patents beschrieben .ist: . -If the 3-chloro-4-oxybenzene-i-arsic acid is replaced in Example 3 the corresponding amount of 3-methyl-q.-oxy'benzene-i-arsinic acid and works otherwise in the same way, 5-methyl-6-oxybenzylphthalimide-3-arsic acid is obtained, which already in example q. of the above-mentioned patent. is:. -
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI31344D DE510449C (en) | 1927-06-01 | 1927-06-01 | Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI31344D DE510449C (en) | 1927-06-01 | 1927-06-01 | Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE510449C true DE510449C (en) | 1930-10-21 |
Family
ID=7187845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI31344D Expired DE510449C (en) | 1927-06-01 | 1927-06-01 | Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivatives |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE510449C (en) |
-
1927
- 1927-06-01 DE DEI31344D patent/DE510449C/en not_active Expired
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