CH193536A - Process for the preparation of bromobenzene-4-azo-3'.5'-diaminopyridine. - Google Patents
Process for the preparation of bromobenzene-4-azo-3'.5'-diaminopyridine.Info
- Publication number
- CH193536A CH193536A CH193536DA CH193536A CH 193536 A CH193536 A CH 193536A CH 193536D A CH193536D A CH 193536DA CH 193536 A CH193536 A CH 193536A
- Authority
- CH
- Switzerland
- Prior art keywords
- diaminopyridine
- azo
- bromobenzene
- preparation
- soluble
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- VNHQEGLPYQLDCV-UHFFFAOYSA-N 2-bromo-5-diazocyclohexa-1,3-diene Chemical compound BrC1=CCC(=[N+]=[N-])C=C1 VNHQEGLPYQLDCV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- ABYXFACYSGVHCW-UHFFFAOYSA-N pyridine-3,5-diamine Chemical compound NC1=CN=CC(N)=C1 ABYXFACYSGVHCW-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Brombenzol-4-azo-3'. 5'-diaminopyridin. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung des stark bac- tericiden Farbstoffes Brombenzol-4-azo-3' . 5'- diaminopyridin. Das Verfahren ist dadurch gekennzeichnet, dass man auf 3. 5-Diamino- pyridin 4-Bromdiazobenzol einwirken lässt. Die neue Verbindung soll als inneres Des infektionsmittel therapeutische Verwendung finden.
<I>Beispiel:</I> 34,4 Teile 4-Bromanilin werden in Schwe felsäure gelöst und unter Kühlung mit einer konzentrierten wässerigen Lösung von 13,8 Teilen Natriumnitrit diazotiert. Diese Lösung wird unter guter Kühlung zu einer Lösung von 21,8 Teilen 3.5-Diaminopyridin in ver dünnter Schwefelsäure zugefügt. Nach einigem Stehen wird unter Kühlung mit Ammoniak alkalisch gemacht, wobei Brombenzol-4-azo- 3' . 5'-diaminopyridin in annähernd quantita tiver Ausbeute ausfällt.
Durch Umkristalli- Bieren aus Methanol oder Äthanol erhält man den neuen Farbstoff in kristalliner Form vom Smp. 210-212 unter Zersetzung. Der Farbstoff ist unlöslich in Wasser, löslich in verdünnten Säuren, schwerlöslich in Äther und Benzol, leichter löslich in Alkoholen und Pyridin.
Process for the preparation of bromobenzene-4-azo-3 '. 5'-diaminopyridine. The present patent relates to a process for the preparation of the strongly bactericidal dye bromobenzene-4-azo-3 '. 5'-diaminopyridine. The process is characterized in that 4-bromodiazobenzene is allowed to act on 3. 5-diaminopyridine. The new compound should find therapeutic use as an internal disinfectant.
<I> Example: </I> 34.4 parts of 4-bromoaniline are dissolved in sulfuric acid and diazotized with a concentrated aqueous solution of 13.8 parts of sodium nitrite while cooling. This solution is added, with good cooling, to a solution of 21.8 parts of 3,5-diaminopyridine in dilute sulfuric acid. After standing for a while, it is made alkaline with ammonia while cooling, bromobenzene-4-azo-3 '. 5'-diaminopyridine precipitates in approximately quantitative yield.
Recrystallization from methanol or ethanol gives the new dye in crystalline form with a melting point of 210-212 with decomposition. The dye is insoluble in water, soluble in dilute acids, sparingly soluble in ether and benzene, more easily soluble in alcohols and pyridine.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH145270T | 1929-11-08 | ||
| DE193536X | 1934-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH193536A true CH193536A (en) | 1937-10-15 |
Family
ID=25714670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH193536D CH193536A (en) | 1929-11-08 | 1935-04-12 | Process for the preparation of bromobenzene-4-azo-3'.5'-diaminopyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH193536A (en) |
-
1935
- 1935-04-12 CH CH193536D patent/CH193536A/en unknown
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