DE840545C - Process for the preparation of azo compounds - Google Patents
Process for the preparation of azo compoundsInfo
- Publication number
- DE840545C DE840545C DEB4457D DEB0004457D DE840545C DE 840545 C DE840545 C DE 840545C DE B4457 D DEB4457 D DE B4457D DE B0004457 D DEB0004457 D DE B0004457D DE 840545 C DE840545 C DE 840545C
- Authority
- DE
- Germany
- Prior art keywords
- solution
- azo compounds
- preparation
- water
- added
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Azoverbindungen Bekanntlich gelangt man durch Einwirkung von diazotiertem Aailin auf Aminopyridine zu Azoverbindungen, die sich als geeignet zur Bekämpfung von Infektionskrankheiten erwiesen haben. Vor allem das unter dein Handelsnamen Pyridium bekannte und in die Therapie eingeführte 3-PheiiyIaZO-2, 6-diaminopyridin zeigt stark bactericide Eigenschaften. Es wurde nun gefunden, daß sich die Diazoverbindung (ICS 2-Aminothiazols leicht mit Aminopyridinen kuppelii läßt, wodurch man züi Azoverbindungen gelangt, welche sowohl gegenüber dein Pyridium als auch gegenüber den Bactericiden der Sulfonamidreihe verbesseite therapeutische Eigenschaften besitzen. Beispiele 1. 17,5 g 2-Aminothiazol werden in 120 CCm Wasser unter Zusatz von 30 ccI" Schwefelsäure konzentriert gelöst und unter Eiskühlung mit 12J g Natriumnitrit, gelöst in wenig Wasser, diazotiert. Man fügt dann eine Lösung von Ig g 2, 6-Diaminopyridin in verdünnter Schwefelsäure hinzu und rührt i Stunde. Hierauf verdünnt man mit der gleichen Raummenge Wasser und fällt den Farbstoff durch Zusatz von wässeriger Ammoniaklösung aus. Der Niederschlag wird abgesatigt, mit Wasser gewaschen und getrocknet. Das Rolierzeugnis schmilzt unter vorherigem Erweichen bei 222 bis 224'. Aus Methanol umkristallisiert, zeigt die Verbindung den Schmelzpunkt 225'. Mit Salzsäure bildet die Azoverbindung ein rötlichbraunes Salz, das in Wasser leicht löslich ist.Process for the preparation of azo compounds It is known that the action of diazotized aailin on aminopyridines leads to azo compounds which have proven to be suitable for combating infectious diseases. In particular, 3-PheiiyIaZO-2,6-diaminopyridine, known under your trade name Pyridium and introduced into therapy, shows strong bactericidal properties. It has now been found that the diazo compound (ICS 2-aminothiazole can easily be coupled with aminopyridines, which leads to azo compounds which have improved therapeutic properties both against pyridium and against the bactericides of the sulfonamide series. Examples 1. 17.5 g 2-aminothiazole are dissolved in 120 cc of water with the addition of 30 CCI "sulfuric acid and concentrated under cooling with ice 12J g of sodium nitrite dissolved in a little water are diazotized. one then adds a solution of Ig g 2, added 6-diaminopyridine in dilute sulfuric acid and The mixture is then diluted with the same volume of water and the dye is precipitated by the addition of aqueous ammonia solution. The precipitate is filtered off, washed with water and dried. The polished product melts, while previously softening, at 222 to 224 °. Recrystallized from methanol, the compound shows the melting point 225. With hydrochloric acid, the azo compound forms a red tan salt that is easily soluble in water.
2. 2,3 g 2-Amino-5-methylthiazol werden in 25 CCM Wasser unter Zusatz von 20 ccm 6 n-Salzsäure gelöst und mit einer wässerigen Lösung von 1,4 9 Natritimnitrit diazotiert. Die Diazoniumsalzlösung wird sodann einer Lösung von 2,1 g 2, 6-Diaminopyridin in 30 ccm 6 n-Salzsäure zugefügt. Nach einigen Stunden wird filtriert und die Azoverbindung aus der Lösung durch Zusatz von verdünnter Natronlauge abgeschieden. Zur Reinigung wird sie in verdünnter Salzsäure gelöst und die Lösung mittels Tierkohle geklärt, worauf nach Filtration wiederum mittels verdünnter Natronlauge gefällt wird. Der Schmelzpunkt der Azoverbindung liegt über 300'. Sie ist unlöslich in den gebräuchlichen organischen Lösungsmitteln.2. 2.3 g of 2-amino-5-methylthiazole are dissolved ccm 6 N hydrochloric acid in 25 cc of water with the addition of 20 and diazotized with an aqueous solution of 1.4 9 Natritimnitrit. The diazonium salt solution is then added a solution of 2.1 g of 2, 6-diaminopyridine in 30 cc of 6N hydrochloric acid. After a few hours, the mixture is filtered and the azo compound is separated out from the solution by adding dilute sodium hydroxide solution. To clean it, it is dissolved in dilute hydrochloric acid and the solution clarified with animal charcoal, whereupon, after filtration, it is again precipitated with dilute sodium hydroxide solution. The melting point of the azo compound is above 300 '. It is insoluble in common organic solvents.
3. Eine durch Umsetzung eines Gemisches von 1,86 g 2-Amin0-5-methylthiaz01-4-carbonsäureäthylester, 30 ccm Wasser und 20 ccm 6 n-Salzsäure mit einer wässerigen Lösung von oß g Natriumnitrit erhaltene Diazoniumsalzlösung wird mit einer salzsauren Lösung von I,1 g 2, 6-Diaminopyridin versetzt, worauf nach einiger Zeit das Kupplungserzeugnis mittels verdünnter Natronlauge ausgefällt wird. Die Abtrennung des Niederschlags und seine Reinigung erfolgen gemäß den Angaben des vorstehenden Beispiels. Die reine Azoverbindung schmilzt unter Zersetzung bei 201'. Sie ist in Alkohol schwer löslich. 3. A by reacting a mixture of 1.86 g of 2-Amin0-5-methylthiaz01-4-carboxylic acid ethyl ester, 30 ml of water and 20 cc of 6 N hydrochloric acid with an aqueous solution of OSS g of sodium nitrite diazonium salt solution is added with a hydrochloric acid solution of 1.1 g of 2,6-diaminopyridine are added, whereupon after some time the coupling product is precipitated using dilute sodium hydroxide solution. The separation of the precipitate and its purification are carried out as described in the previous example. The pure azo compound melts at 201 'with decomposition. It is sparingly soluble in alcohol.
4. 1,53 g 2, 6-Diaminopyridin-4-carbonsäure werden in Wasser unter Zusatz von 15 ccm 2 n-Natronlauge gelöst. Die Lösung wird unter Eiskühlung mit einer Diazoniumsalzlösung aus i g 2-Aminothiazol versetzt. Nach einigen Stunden wird 5o','"ige Essigsäure hinzugefügt und der Niederschlag abgesaugt. Die so erhaltene Azoverbindung ist gleichfalls in organischen Lösungsmitteln fast unlöslich.4. 1.53 g of 2,6-diaminopyridine-4-carboxylic acid are dissolved in water with the addition of 15 ccm of 2N sodium hydroxide solution. A diazonium salt solution of 1 g of 2-aminothiazole is added to the solution while cooling with ice. After a few hours, 50% acetic acid is added and the precipitate is filtered off with suction. The azo compound thus obtained is also almost insoluble in organic solvents.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB4457D DE840545C (en) | 1942-10-25 | 1942-10-25 | Process for the preparation of azo compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB4457D DE840545C (en) | 1942-10-25 | 1942-10-25 | Process for the preparation of azo compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE840545C true DE840545C (en) | 1952-06-03 |
Family
ID=6953667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB4457D Expired DE840545C (en) | 1942-10-25 | 1942-10-25 | Process for the preparation of azo compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE840545C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE952017C (en) * | 1953-10-15 | 1956-11-08 | Bayer Ag | Process for the preparation of water-insoluble monoazo dyes |
| US2783224A (en) * | 1955-08-18 | 1957-02-26 | Nepera Chemical Co Inc | Salts of 2, 6-diamino-3-phenylazo-pyridine |
| DE963176C (en) * | 1954-07-05 | 1957-05-02 | Basf Ag | Process for the production of azo dyes |
| EP0135131A1 (en) * | 1983-08-20 | 1985-03-27 | BASF Aktiengesellschaft | Azo dyestuffs of the isothiazole series |
-
1942
- 1942-10-25 DE DEB4457D patent/DE840545C/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE952017C (en) * | 1953-10-15 | 1956-11-08 | Bayer Ag | Process for the preparation of water-insoluble monoazo dyes |
| DE963176C (en) * | 1954-07-05 | 1957-05-02 | Basf Ag | Process for the production of azo dyes |
| US2783224A (en) * | 1955-08-18 | 1957-02-26 | Nepera Chemical Co Inc | Salts of 2, 6-diamino-3-phenylazo-pyridine |
| EP0135131A1 (en) * | 1983-08-20 | 1985-03-27 | BASF Aktiengesellschaft | Azo dyestuffs of the isothiazole series |
| US4774324A (en) * | 1983-08-20 | 1988-09-27 | Basf Aktiengesellschaft | Isothiazolylazo dyes |
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