DE235051C - - Google Patents
Info
- Publication number
- DE235051C DE235051C DENDAT235051D DE235051DA DE235051C DE 235051 C DE235051 C DE 235051C DE NDAT235051 D DENDAT235051 D DE NDAT235051D DE 235051D A DE235051D A DE 235051DA DE 235051 C DE235051 C DE 235051C
- Authority
- DE
- Germany
- Prior art keywords
- alkali
- compound
- sodium
- sulfonic acid
- thiazole
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 150000003557 thiazoles Chemical class 0.000 claims description 2
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- -1 sulfonic acids aromatic amines Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- AKHNMLFCWUSKQB-UHFFFAOYSA-L Sodium thiosulphate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- RIDNBUBZBRPJEY-UHFFFAOYSA-N NC=1N=C(SC1)S(=O)(=O)O Chemical class NC=1N=C(SC1)S(=O)(=O)O RIDNBUBZBRPJEY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Λ! 235051 — KLASSE \2p. GRUPPE - Λ! 235051 - CLASS \ 2p. GROUP
Zusatz zum Patente 165126 vom, 14. Mai 1904.*)Addendum to patent 165126 of May 14, 1904. *)
Patentiert im Deutschen Reiche vom 6. April 1910 ab. Längste Dauer: 13.Mai 1919.Patented in the German Empire on April 6, 1910. Longest duration: May 13, 1919.
Durch die Patente 165126 und 165127, Kl. 12 p, sind Verfahren zur Darstellung von Sulfosäuren der Thiazolreihe geschützt, die darin bestehen, daß man entweder auf die aus aromatischen Aldehyden und den Sulfosäuren aromatischer Amine oder ihren Derivaten erhältlichen Kondensationsprodukte oder unmittelbar auf das Gemenge der Komponenten Alkalipolysulfide einwirken läßt bzw. die entsprechenden Benzylderivate in dieser Weise behandelt.Through patents 165126 and 165127, Kl. 12 p, processes for the preparation of sulfonic acids of the thiazole series are protected consist of either the aromatic aldehydes or the sulfonic acids aromatic amines or their derivatives available condensation products or directly on the mixture of components Alkali polysulphides can act or the corresponding benzyl derivatives in this way treated.
Es wurde nun gefunden, daß man derartige Thiazosulfosäuren auch dadurch erhalten kann, daß man die in den genannten Verfahren verwendeten Alkalipolysulfide durch Alkalithiosulfate ersetzt. Zum Unterschied von dem Verfahren des Hauptpatents und seines Zusatzes erhält man nach dem vorliegenden Verfahren bei Verwendung von Nitrobenzyliden- bzw. Nitrobenzylverbindungen die entsprechenden Nitroverbindungen, die man dann weiter zu den Aminothiazolsulfosäuren reduzieren kann. ,It has now been found that such thiazosulfonic acids can also be obtained by that the alkali polysulphides used in the processes mentioned are replaced by alkali thiosulphates replaced. In contrast to the process of the main patent and its addition, one obtains according to the present process when using nitrobenzylidene or nitrobenzyl compounds, the corresponding Nitro compounds, which are then further reduced to the aminothiazole sulfonic acids can. ,
2- Beispiel 1. 2 - example 1.
22,5 kg 2-Amino-5-oxynäphtalin-7-sulfosäure werden mit 10,6 kg Benzaldehyd nach dem Verfahren des Hauptpatents zur Benzylidenverbindung kondensiert. Hierauf wird die so erhaltene Verbindung mit 100 kg Natriumthiosulfat in einem Gesamtvolumen von 1001 3522.5 kg of 2-amino-5-oxynäphtalin-7-sulfonic acid are mixed with 10.6 kg of benzaldehyde according to the Process of the main patent condensed to the benzylidene compound. Then it becomes like that obtained compound with 100 kg of sodium thiosulfate in a total volume of 1001 35
15 bis 20 Stunden gekocht. Die gebildete Thiazolverbindung wird durch Aussalzen mit Hilfe von Kochsalz isoliert und durch Umlösen gereinigt. Das so erhältliche Natriumsalz ist ein schwach braunes· Pulver, das sich in Wasser leicht löst, in Alkohol schwer löslich, in Äther und Benzol unlöslich ist. Die durch Ansäuern erhältliche freie Säure, die schwach gelb gefärbt ist, löst sich schwer in Wasser und leicht in Alkalien auf.Cooked for 15 to 20 hours. The thiazole compound formed is by salting out with Isolated using table salt and purified by dissolving. The sodium salt thus obtainable is a pale brown powder that dissolves easily in water, sparingly soluble in alcohol, in ether and benzene is insoluble. The free acid obtained by acidification, which is pale yellow in color is difficult to dissolve in water and easily in alkalis.
Die Benzylidenverbindung aus 26 kg 2-Amino-8-oxynaphtalin-6-sulfosäure und 15,1 kg m-Nitrobenzaldehyd wird mit 100 kg Natriumthiosulfat in einer Verdünnung von 100 1 gekocht. Nach etwa 15 bis 20 Stunden ist.die Reaktion beendet. Beim Ansäuern und auf Zusatz von etwas Kochsalz fällt die Thiazolverbindung aus. Die so erhältliche Thiazolverbindung ist als Natriumsalz ein gelbes Pulver. Die freie Säure ist rotbraun gefärbt. Das Natriumsalz ist löslich in Wasser, schwer löslich in Alkohol und unlöslich in Benzol und Äther. Durch Reduktion gelangt man zu der entsprechenden Aminothiazolsulfosäure.The benzylidene compound from 26 kg of 2-amino-8-oxynaphthalene-6-sulfonic acid and 15.1 kg of m-nitrobenzaldehyde is mixed with 100 kg of sodium thiosulfate cooked in a dilution of 100 1. The reaction occurs after about 15 to 20 hours completed. The thiazole compound falls on acidification and when a little table salt is added the end. The thiazole compound thus obtainable is a yellow powder as the sodium salt. The free Acid is red-brown in color. The sodium salt is soluble in water and sparingly soluble in alcohol and insoluble in benzene and ether. Reduction leads to the corresponding one Aminothiazole sulfonic acid.
4545
5555
26 kg 2-amino-5-oxynaphtalin-7-sulfosaures Natrium werden unter Zusatz von essigsaurem Natrium mit 12,6 kg Benzylchlorid zur Ben-26 kg of 2-amino-5-oxynaphthalene-7-sulfonic acid sodium are added with acetic acid Sodium with 12.6 kg benzyl chloride for ben-
*) Früheres Zusatzpatent 165127.*) Former additional patent 165127.
zylaminonaphtol-7-sulfosäure kondensiert. Diese Verbindung wird darauf mit 20 kg Natriumthiosulfat in einem Volumen von 15 1 am Rückflußkühler gekocht. Nach Vollendung der Reaktion wird die Thiazolverbindung durch Schwefelsäure abgeschieden und über das Natriumsalz gereinigt.zylaminonaphthol-7-sulfonic acid condensed. This compound is then added with 20 kg of sodium thiosulphate Boiled in a volume of 15 l on the reflux condenser. After completion the reaction becomes the thiazole compound deposited by sulfuric acid and purified over the sodium salt.
An Stelle von Benzylchlorid kann man auch Nitrobenzylchlorid verwenden.Instead of benzyl chloride, nitrobenzyl chloride can also be used.
Das Verfahren verläuft in analoger Weise bei Verwendung anderer Benzyliden- bzw. Benzylverbindungen oder von Mischungen aus den Aldehyden mit den Aminosulfosäuren.The process proceeds in an analogous manner when using other benzylidene or Benzyl compounds or mixtures of the aldehydes with the aminosulfonic acids.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE235051C true DE235051C (en) |
Family
ID=494871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT235051D Active DE235051C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE235051C (en) |
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0
- DE DENDAT235051D patent/DE235051C/de active Active
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