CH311468A - Process for the preparation of a derivative of 1-amino-naphthalene-4-sulfonic acid. - Google Patents
Process for the preparation of a derivative of 1-amino-naphthalene-4-sulfonic acid.Info
- Publication number
- CH311468A CH311468A CH311468DA CH311468A CH 311468 A CH311468 A CH 311468A CH 311468D A CH311468D A CH 311468DA CH 311468 A CH311468 A CH 311468A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- sulfonic acid
- naphthalene
- diamine
- acid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
Description
Verfahren zur Herstellung eines Derivates der l-Amino-naphthalin-4-sulfonsäure.
Es wurde gefunden, dass man eine Verbindung der Formel
EMI1.1
erhalten kann, wenn man 1-Chlor-naphthalin 4-sulfonsäure mit Di- (ss-amino-äthyl)-amin unter solchen Bedingungen umsetzt, dass nur eine Aminogruppe des Diamins mit dem Chloratom der Chlornaphthalinsulfonsäure reagiert.
Die nach dem vorliegenden Verfahren erhaltene nene Verbindung der Formel (1) lässt sich aus Wasser umkristallisieren. Gut umkristallisierbar aus Wasser ist auch das in Na triumcarbonatlosung entstehende Natriumsalz der Sulfonsäure. Sehr leicht löslich ist die SÏure in 2 Äquivalenten und mehr Natronlauge.
Mit p-Nitro-benzoldiazoniumchlorid kuppelt clie Base zu einem tief violetten Farbstoff.
Die vorliegende Real : tion wird zweck mässig so geleitet, dass ein erheblicher Über- schuss an Diamin während der Reaktion vorliegt. Die Umsetzung wird mit Vorteil bei der Siedetemperatur des Diamins, also bei etwa 190 , durchgeführt.
Beispiel :
36,5 Teile 1-Chlor-naphthalin-4-sulfonsÏure (1 Mol = 242, 6 g) werden als Natriumsalz in 103 Teilen Di- (-amino-äthyl)- amin 20 Stunden unter Rückfluss gekocht. Die in der Masse gemessene Temperatur beträgt etwa 190 und steigt während des Kochens um einige Grade. Dann wird das nicht ver brauchte Di- (-amino-äthyl)-anün im Vakuum abdestilliert. Der Destillationsrückstand wird in etwa 500 Raumteilen 3% iger Natrium hydroxydlösung gelöst und durch Zugabe von Salzsäure deutlich sauer gegen Kongopapier gestellt. Die in guter Ausbeute ausgefällte Verbindung der Formel (1) wird abfiltriert und getrocknet.
PATENTANSPRUCH :
Verfahren zur Herstellung eines Derivates der 1-Amino-naphthalin-4-sulfonsäure, dadurch gekennzeichnet, dass man 1-Chlor-naph- thalin-4-sulfonsäure mit Di- (-amino-äthyl)- amin unter solchen Bedingungen umsetzt, dass nur eine Aminogruppe des Diamins mit dem Chloratom der Chlornaphthalinsulfonsäure reagiert.
Die erhaltene neue Verbindung entspricht der Formel (1) und lässt sich aus Wasser um
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a derivative of 1-amino-naphthalene-4-sulfonic acid.
It has been found that one can obtain a compound of the formula
EMI1.1
can be obtained if 1-chloro-naphthalene-4-sulfonic acid is reacted with di- (s-amino-ethyl) -amine under such conditions that only one amino group of the diamine reacts with the chlorine atom of the chloronaphthalenesulfonic acid.
The compound of the formula (1) obtained by the present process can be recrystallized from water. The sodium salt of sulfonic acid formed in sodium carbonate solution can also be recrystallized from water. The acid is very easily soluble in 2 equivalents or more of sodium hydroxide solution.
The base couples with p-nitro-benzene diazonium chloride to form a deep violet dye.
The present implementation is expediently conducted in such a way that there is a considerable excess of diamine during the reaction. The reaction is advantageously carried out at the boiling point of the diamine, i.e. around 190.
Example:
36.5 parts of 1-chloro-naphthalene-4-sulfonic acid (1 mol = 242.6 g) are refluxed as the sodium salt in 103 parts of di- (-amino-ethyl) -amine for 20 hours. The temperature measured in the mass is about 190 and increases a few degrees during cooking. Then the unused di- (amino-ethyl) -anün is distilled off in vacuo. The distillation residue is dissolved in about 500 parts by volume of 3% sodium hydroxide solution and made significantly acidic against Congo paper by adding hydrochloric acid. The compound of the formula (1) which has precipitated out in good yield is filtered off and dried.
PATENT CLAIM:
Process for the preparation of a derivative of 1-amino-naphthalene-4-sulfonic acid, characterized in that 1-chloro-naphthalene-4-sulfonic acid is reacted with di- (-amino-ethyl) - amine under such conditions that only an amino group of the diamine reacts with the chlorine atom of the chloronaphthalenesulfonic acid.
The new compound obtained corresponds to the formula (1) and can be converted from water
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH748715X | 1952-08-28 | ||
CH311468T | 1952-12-24 | ||
CH775885X | 1953-07-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311468A true CH311468A (en) | 1955-11-30 |
Family
ID=27178334
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311468D CH311468A (en) | 1952-08-28 | 1952-12-24 | Process for the preparation of a derivative of 1-amino-naphthalene-4-sulfonic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH311468A (en) |
-
1952
- 1952-12-24 CH CH311468D patent/CH311468A/en unknown
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