AT152825B - Process for the preparation of basic substituted aminoazo compounds. - Google Patents
Process for the preparation of basic substituted aminoazo compounds.Info
- Publication number
- AT152825B AT152825B AT152825DA AT152825B AT 152825 B AT152825 B AT 152825B AT 152825D A AT152825D A AT 152825DA AT 152825 B AT152825 B AT 152825B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- aminoazo compounds
- basic substituted
- methyl
- aminoazo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 aminoazo compounds Chemical class 0.000 title description 5
- 239000002253 acid Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JRYPELJRMROVBP-UHFFFAOYSA-N 2-chloro-5-diazocyclohexa-1,3-diene Chemical compound ClC1=CCC(=[N+]=[N-])C=C1 JRYPELJRMROVBP-UHFFFAOYSA-N 0.000 description 1
- VOXCBGXOKNLLKT-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1 VOXCBGXOKNLLKT-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000019693 cherries Nutrition 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
- 239000013078 crystal Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung basisch substituierter Aminoazoverbindungen.
EMI1.1
<Desc/Clms Page number 2>
Beispiel 2 : 49 g 4'-Ch or-2-methyl-4-aminoazobenzol [aus Methylalkohol braunrote-Nadeln vom F = 920 erhalten durch Kuppeln von 4-Chlor-l-diazobenzol mit m-Toluidin] werden mit 35 g salzsaurem Salz des < .-Methyl-S-diäthylaminobutylesters der p-Toluolsulfonsäure {erhalten durch Umsetzen von p-Toluolsulfonsäurechlorid mit 5-Diäthylaminopentanol-(2) [s. Patentschrift Nr. 118738]
EMI2.1
wodurch das nicht umgesetzte 4'-Chlor-2-methyl-4-aminoazobenzol als freie Base abgeschieden wird, die mit Äther oder Benzol ausgeschüttelt werden kann.
Das entstandene 4'-Chlor-2-methyl-4- [a-Methyl- #-diäthylaminobutylamino]-azobenzol, das als Salz in Lösung bleibt, wird durch Zugabe von Natronlauge abgeschieden, mit Äther ausgeschüttelt und mit einer ätherischen Chlorwasserstofflösung in das salzsaure Salz umgewandelt. Dieses bildet rotgrün schillernde Kristalle vom F = 131 , die sich in Wasser mit orangegelber Farbe leicht lösen ; die Lösung wird durch Mineralsäuren kirschrot gefärbt.
PATENT-ANSPRÜCHE :
1. Verfahren zur Darstellung basisch substituierter Aminoazoverbindungen, dadurch gekenn-' zeichnet, dass man auf'Aminoazoverbindungen der allgemeinen Formel R. N : N. R'. NHR" (worin R einen aromatischen, heterocyclischen oder aromatisch-heterocyclischen Rest, R'einen Rest der Benzolreihe und N'einen beliebigen einwertigen Rest oder Wasserstoff bedeuten) reaktionsfähige Ester aliphatischer Aminoalkohole einwirken lässt.
<Desc / Clms Page number 1>
Process for the preparation of basic substituted aminoazo compounds.
EMI1.1
<Desc / Clms Page number 2>
Example 2: 49 g of 4'-Ch or-2-methyl-4-aminoazobenzene [obtained from methyl alcohol red-brown needles with F = 920 by coupling 4-chloro-1-diazobenzene with m-toluidine] are mixed with 35 g of hydrochloric acid of the <. -methyl-S-diethylaminobutyl ester of p-toluenesulfonic acid {obtained by reacting p-toluenesulfonic acid chloride with 5-diethylaminopentanol- (2) [s. Patent No. 118738]
EMI2.1
whereby the unreacted 4'-chloro-2-methyl-4-aminoazobenzene is deposited as a free base, which can be extracted with ether or benzene.
The resulting 4'-chloro-2-methyl-4- [a-methyl- # -diethylaminobutylamino] -azobenzene, which remains in solution as a salt, is deposited by adding sodium hydroxide solution, extracted with ether and mixed with an ethereal hydrogen chloride solution into the hydrochloric acid Converted to salt. This forms shimmering red-green crystals of F = 131, which easily dissolve in water with an orange-yellow color; the solution is colored cherry red by mineral acids.
PATENT CLAIMS:
1. Process for the preparation of basic substituted aminoazo compounds, characterized in that one is based on aminoazo compounds of the general formula R. N: N. R '. NHR "(where R is an aromatic, heterocyclic or aromatic-heterocyclic radical, R 'is a radical of the benzene series and N' is any monovalent radical or hydrogen) allows reactive esters of aliphatic amino alcohols to act.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE152825X | 1931-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT152825B true AT152825B (en) | 1938-03-10 |
Family
ID=5675286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT152825D AT152825B (en) | 1931-11-07 | 1932-11-03 | Process for the preparation of basic substituted aminoazo compounds. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT152825B (en) |
-
1932
- 1932-11-03 AT AT152825D patent/AT152825B/en active
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