CH185602A - Process for producing an azo compound. - Google Patents
Process for producing an azo compound.Info
- Publication number
- CH185602A CH185602A CH185602DA CH185602A CH 185602 A CH185602 A CH 185602A CH 185602D A CH185602D A CH 185602DA CH 185602 A CH185602 A CH 185602A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- acid
- acid amide
- azo compound
- olive
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- -1 azo compound Chemical class 0.000 title claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- XZMIAZCXISFPEJ-UHFFFAOYSA-N 4-aminobenzenesulfonamide;hydrochloride Chemical compound Cl.NC1=CC=C(S(N)(=O)=O)C=C1 XZMIAZCXISFPEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer Azoverbindung. Das Hauptpatent betrifft ein Verfahren zur Herstellung einer Azoverbindung, die sich durch ihre bakterizide Wirkung aus zeichnet.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des 2-Amino 4-ogy-azobenzol-5-sulfonsäure-4'-sulfonsäure- amids, das ebenfalls eine bakterizide Wir kung aufweist. Das Verfahren ist dadurch gekennzeichnet, dass man die Diazoverbin- dung des 4-Aminobenzolsulfonsäureamids mit 3-Aminophenol-6-sulfonsäure kuppelt. Die Kupplung erfolgt zweckmässig unter Verwendung einer alkalischen Lösung der 3 Aminophenol-6-sulfonsäure.
Aus -der alkali schen Reaktionslösung wird die neue Ver bindung durch verdünnte Säuren, zum Bei spiel Salzsäure, abgeschieden.
Das so erhältliche 2-Amino-4-ogy-azo- benzol-5-sulfonsäure-4'-sulfonsäureamid bil det ein olivgrün gefärbtes Pulver, das sich in Wasser leicht mit olivgrüner-Farbe, in Natriumkarbonatlösung mit orangegelber Farbe löst.
Die neue Verbindung soll therapeutische Verwendung finden. <I>Beispiel:</I> 2,0,8 g Hydrochlorid des 4-Aminobenzol- sulfonsäureamids werden diazotiert und mit einer alkalischen Lösung von 1$,9 g 3- Aminophenol-6-sulfonsäure versetzt. Aus der gelbroten Lösung wird durch verdünnte Salzsäure die Azoverbindung als brauner Niederschlag gewonnen.
Dieser wird in ver dünnter Natriumkarbonatlösung unter schwa chem Erwärmen gelöst und durch Zugabe von Essigsäure und Natriumchloridlösung das 2-Amino-4-ogyazobenzol-5-sulfonsäure-4'- sulfonsäureamid als olivgrün gefärbtes Pul ver gefällt. Es löst sich in Wasser sehr leicht mit olivgrüner Farbe, in Natriumkarbonat lösung orangegelb; durch Salzsäure wird die. Azoverbindung ausgefällt.
Process for producing an azo compound. The main patent relates to a process for the production of an azo compound, which is characterized by its bactericidal effect.
The subject of the present patent is a method for the preparation of the 2-amino 4-ogy-azobenzene-5-sulfonic acid-4'-sulfonic acid amide, which also has a bactericidal effect. The process is characterized in that the diazo compound of the 4-aminobenzenesulfonic acid amide is coupled with 3-aminophenol-6-sulfonic acid. The coupling is conveniently carried out using an alkaline solution of the 3 aminophenol-6-sulfonic acid.
The new compound is separated from the alkaline reaction solution using dilute acids such as hydrochloric acid.
The 2-amino-4-ogy-azobenzene-5-sulfonic acid-4'-sulfonic acid amide which can be obtained in this way forms an olive-green colored powder that dissolves easily in water with an olive-green color and in sodium carbonate solution with an orange-yellow color.
The new compound should find therapeutic use. <I> Example: </I> 2.0.8 g of 4-aminobenzenesulfonic acid amide hydrochloride are diazotized and an alkaline solution of 1.9 g of 3-aminophenol-6-sulfonic acid is added. The azo compound is obtained as a brown precipitate from the yellow-red solution using dilute hydrochloric acid.
This is dissolved in dilute sodium carbonate solution with weak warming and the 2-amino-4-ogyazobenzene-5-sulfonic acid-4'-sulfonic acid amide is precipitated as an olive-green colored powder by adding acetic acid and sodium chloride solution. It dissolves very easily in water with an olive-green color, in sodium carbonate solution it dissolves orange-yellow; by hydrochloric acid the. Azo compound precipitated.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH173540T | 1933-12-16 | ||
| DE185602X | 1934-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185602A true CH185602A (en) | 1936-07-31 |
Family
ID=25719373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185602D CH185602A (en) | 1933-12-16 | 1935-03-16 | Process for producing an azo compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185602A (en) |
-
1935
- 1935-03-16 CH CH185602D patent/CH185602A/en unknown
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