CH171983A - Process for the preparation of an azo compound. - Google Patents
Process for the preparation of an azo compound.Info
- Publication number
- CH171983A CH171983A CH171983DA CH171983A CH 171983 A CH171983 A CH 171983A CH 171983D A CH171983D A CH 171983DA CH 171983 A CH171983 A CH 171983A
- Authority
- CH
- Switzerland
- Prior art keywords
- red
- methyl
- iodo
- azobenzene
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 azo compound Chemical class 0.000 title claims 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
- 239000002253 acid Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 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'-jod-4-(N- [r-amino-p-oxy-a- propyl] - äthyl- amino)-azobenzolhydrochlorids. Dieses Ver fahren ist dadurch gekennzeichnet, dass man auf das 2-Methyl-4'-jod-4-(epihydryl-äthyl- amino)-azobenzol Ammoniak, zweckmässig un ter Erwärmen, einwirken lässt und das Reak tionsprodukt mittelst Salzsäure in das Hydro- chlorid verwandelt.
Das so erhältliche 2-Methyl-4'-jod-4-(N- (r-amino-p-oxy-a-pr#opyll -äthylamino)-azo- benzolhydrochlorid bildet braunrote Nadeln vorn Schmelzpunkt<B>1980,</B> die sich in Wasser kirschrot, in verdünnter Mineralsäure rotvio lett lösen.
Das neue Produkt soll therapeutische An wendung finden.
<I>Beispiel:</I> 2-Methyl-4'-jod-4-(epihydryl-äthylamino)- azobenzol vorn F.<B>117',</B> hellbraune, rotschil- lernde Prismen, erhalten durch Diazotieren von 21,9 gr 4-Jodanilin mit 7 gr Natriumnitrit und Kuppeln der Diazoverbindung mit<B>19,1</B> gr N-Epihydryläthyl-3-toluidin (KP;<B>1330)</B> in essigsaurer Lösung, wird mit überschüssigem methylalkoholischem Ammoniak 2 Stunden im Bombenrohr auf 100 erhitzt.
Darauf wer den Methylalkohol und Ammoniak abgedampft und das gebildete 2-Methyl-4'-jod-4-(N- [r ami iro-ss-oxy-a-propylj -äthylamino)-azobenzol mittelst Salzsäure in das Hydrochlorid um gewandelt. Das letztere bildet braunrote Na deln vom Schmelzpunkt<B>198',</B> die kirschrot in Wasser und rotviolett in Mineralsäuren löslich sind.
Process for the preparation of an azo compound. The present patent relates to a process for the preparation of 2-methyl-4'-iodo-4- (N- [r-amino-p-oxy-a-propyl] -ethyl-amino) -azobenzene hydrochloride. This process is characterized in that ammonia is allowed to act on the 2-methyl-4'-iodo-4- (epihydryl-ethyl-amino) -azobenzene, expediently under heating, and the reaction product is converted into the hydrochloric acid converted to chloride.
The 2-methyl-4'-iodo-4- (N- (r-amino-p-oxy-a-propyl-ethylamino) -azobenzene hydrochloride thus obtainable forms brown-red needles with a melting point of 1980, B> which dissolve cherry-red in water and red-purple in dilute mineral acid.
The new product is intended to find therapeutic applications.
<I> Example: </I> 2-methyl-4'-iodo-4- (epihydryl-ethylamino) - azobenzene in front of F. <B> 117 ', </B> light brown, red shimmering prisms, obtained by diazotization of 21.9 g of 4-iodoaniline with 7 g of sodium nitrite and coupling of the diazo compound with <B> 19.1 </B> g of N-epihydrylethyl-3-toluidine (KP; <B> 1330) </B> in acetic acid solution , is heated to 100 with excess methyl alcoholic ammonia for 2 hours in a sealed tube.
The methyl alcohol and ammonia are then evaporated and the 2-methyl-4'-iodo-4- (N- [r ami iro-ss-oxy-a-propylj -ethylamino) azobenzene is converted into the hydrochloride using hydrochloric acid. The latter forms brown-red needles with a melting point of <B> 198 ', </B> which are cherry-red in water and red-violet in mineral acids.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE171983X | 1931-11-07 | ||
| CH170235T | 1932-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH171983A true CH171983A (en) | 1934-09-15 |
Family
ID=25718901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH171983D CH171983A (en) | 1931-11-07 | 1932-11-05 | Process for the preparation of an azo compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH171983A (en) |
-
1932
- 1932-11-05 CH CH171983D patent/CH171983A/en unknown
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