CH171984A - Process for the preparation of an azo compound. - Google Patents
Process for the preparation of an azo compound.Info
- Publication number
- CH171984A CH171984A CH171984DA CH171984A CH 171984 A CH171984 A CH 171984A CH 171984D A CH171984D A CH 171984DA CH 171984 A CH171984 A CH 171984A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo compound
- azobenzene
- sulfamide
- ammonia
- hydrochloride
- Prior art date
Links
- -1 azo compound Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer Azoverbindung. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des 2-Methyl 4'-sulfaniid-4-(N-[r-amino-,3-oxy-a-propyl]- ätliylamino)-azobenzolhydi-ochlorides. DasVer- fahren ist dadurch gekennzeichnet, dass man auf das 2-Methyl-4'-sulfamid-4-(epihydryl- ätliylamino)-azobenzol Ammoniak, zweck mässig unter Erwärmen, einwirken lässt und das Reaktionsprodukt mittelst Salzsäure in das Hydrochlorid umwandelt.
Das so erhältliche 2-Methyl-4'-sulfamid- 4- (N- [r- ainino-p- oxy-a-propylj - äthylamino)- azobenzolhydrochlorid bildet zinnoberrote Kri stalle vom Schmelzpunkt 2121, die sich in Wasser mit gleicher Farbe lösen. Die Azo- verbindung ist auch in verdünnter Natron lauge löslich, in Natriumkarbonatlösung da gegen unlöslich.
Das neue Produkt soll therapeutische Anwendung finden. Beispiel: 2-AZethyl.4'- sulfamid-4-(epibydryl-äthyl- amino)-azobenzol vom F. 12111, ziegelrote Kri stalle, erhalten durch Diazotieren von 17,1 gr 4-Amiriobenzolstilfamid mit 7 gr Natriumnitrit und Kuppeln der Diazoverbindung mit 19,1 gr N-Epihydryläthyl-3-toluidin (Kp7 133 ) in essigsaurer Lösung,
wird mit überschüssigem methylalkoholischem Ammoniak 2 Stunden im Bombenrohr auf 100 erhitzt. Darauf werden Methylalkohol und Ammoniak abgedampft und das gebildete 2-Methyl-4'-sulfamid-4-(N- [r - amino-i3- oxy- a-propyl] - äthylamino) - azo- benzol mittelst Salzsäure in das Hydrochlorid umgewandelt. Das letztere bildet zinnoberrote Kristalle vom Schmelzpunkt 212 , die sich in Wasser mit gleicher Farbe lösen.
Die Azo- verbindung ist auch in verdünnter Natron lauge löslich, in Natriumkarbonatlösung da gegen unlöslich.
Process for the preparation of an azo compound. The subject of the present patent is a process for the preparation of the 2-methyl 4'-sulfaniid-4- (N- [r-amino-, 3-oxy-a-propyl] -ätliylamino) -azobenzolhydi-ochlorides. The process is characterized in that ammonia is allowed to act on the 2-methyl-4'-sulfamide-4- (epihydryl-ätliylamino) -azobenzene, advantageously with heating, and the reaction product is converted into the hydrochloride using hydrochloric acid.
The 2-methyl-4'-sulfamide-4- (N- [r-ainino-p-oxy-a-propylj-ethylamino) -azobenzene hydrochloride thus obtainable forms vermilion crystals with a melting point of 2121, which dissolve in water with the same color . The azo compound is also soluble in dilute sodium hydroxide solution, but insoluble in sodium carbonate solution.
The new product should find therapeutic application. Example: 2-AZethyl.4'-sulfamid-4- (epibydryl-ethyl-amino) -azobenzene from F. 12111, brick-red crystals, obtained by diazotizing 17.1 g of 4-amiriobenzolstilfamide with 7 g of sodium nitrite and coupling the diazo compound with 19.1 g of N-epihydrylethyl-3-toluidine (Kp7 133) in acetic acid solution,
is heated to 100 for 2 hours in a sealed tube with excess methyl alcoholic ammonia. Methyl alcohol and ammonia are then evaporated off and the 2-methyl-4'-sulfamide-4- (N- [r - amino-13-oxy-a-propyl] - ethylamino) azobenzene formed is converted into the hydrochloride using hydrochloric acid. The latter forms vermilion crystals with a melting point of 212, which dissolve in water of the same color.
The azo compound is also soluble in dilute sodium hydroxide solution, but insoluble in sodium carbonate solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE171984X | 1931-11-07 | ||
| CH170235T | 1932-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH171984A true CH171984A (en) | 1934-09-15 |
Family
ID=25718902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH171984D CH171984A (en) | 1931-11-07 | 1932-11-05 | Process for the preparation of an azo compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH171984A (en) |
-
1932
- 1932-11-05 CH CH171984D patent/CH171984A/en unknown
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