CH175234A - Process for the preparation of 4-amino-3-ethoxy-4'-methoxy-diphenylamine. - Google Patents
Process for the preparation of 4-amino-3-ethoxy-4'-methoxy-diphenylamine.Info
- Publication number
- CH175234A CH175234A CH175234DA CH175234A CH 175234 A CH175234 A CH 175234A CH 175234D A CH175234D A CH 175234DA CH 175234 A CH175234 A CH 175234A
- Authority
- CH
- Switzerland
- Prior art keywords
- diphenylamine
- methoxy
- amino
- preparation
- ethoxy
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 239000012021 ethylating agents Substances 0.000 claims description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
- -1 amino compound Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 229940008406 diethyl sulfate Drugs 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Verfahren zur Darstellung des 4-Amino-3-äthogy-4'-methoxy-diphenylamins. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Darstellung des 4-Amino-3-äthoxy-4'-methoxy-diphenyl- amins, welches dadurch gekennzeichnet ist, dass man 4-Acetylamino-3-oxy-4'-methoxy- diphenylamin mit einem äthylierenden Mittel behandelt und sodann das so erhaltene 4-Ace- tylamino- 3 -äthoxy-4'-methoxy-diphenylamin durch Verseifen in die freie Aminoverbin- dung überführt.
Die so erhaltene neue Verbindung soll als Zwischenprodukt für die Herstellung von Farbstoffen Verwendung finden.
Beispiel: 27,2 Gewichtsteile 4-Acetylamino-3-oxy- 4'-methoxy-diphenylamin (erhalten durch Nitrosieren von 3-Oxy-4'-methoxy-diphenyl- a.min zum 3-Oxy-4'-methoxy-N-nitroso-di- phenylamin, Umlagern zum 4-Nitroso-3-oxy- 4'-methoxy-diphenylamin, Reduzieren und Acetylieren zum 4-Acetylamino-3-oxy-4'me- thoxy-diphenylamin)
werden in 150 Volum- teilen Alkohol und 25 Volumteilen 31%iger Natronlauge gelöst, auf 50 C erwärmt und bei 50 bis 55 C innerhalb 15 Minuten mit 20 Gewichtsteilen Diäthylsulfat versetzt und noch weitere 15 Minuten auf etwa<B>60'</B> C ge halten. Die so erhaltene klare Lösung wird mit der gleichen Menge Wasser verdünnt, wodurch sich das 4-Acetylamino-3-äthoxy-4'- methoxy-diphenylamin kristallin ausscheidet.
Das wie üblich isolierte und durch Um kristallisieren gereinigte Produkt wird zur Verseifung der Acetylgruppe 3 Stunden mit 75 Volumteilen Alkohol und 25 Volumteilen 20%iger Salzsäure gekocht. Aus der so er haltenen Lösung kristallisiert beim Erkalten das salzsaure Salz des 4-Amino-3-äthoxy-4'- methoxy-diphenyl.amins aus. Die freie Base kristallisiert aus Cyclohexan in farblosen Blättchen vom Schmelzpunkt 74 bis 75 C (unkorrigiert).
Process for the preparation of 4-amino-3-ethogy-4'-methoxy-diphenylamine. The subject of the present additional patent is a process for the preparation of 4-amino-3-ethoxy-4'-methoxy-diphenylamine, which is characterized in that 4-acetylamino-3-oxy-4'-methoxy-diphenylamine with treated with an ethylating agent and then the 4-acetylamino-3-ethoxy-4'-methoxy-diphenylamine thus obtained is converted into the free amino compound by saponification.
The new compound obtained in this way is said to be used as an intermediate for the preparation of dyes.
Example: 27.2 parts by weight of 4-acetylamino-3-oxy-4'-methoxy-diphenylamine (obtained by nitrosating 3-oxy-4'-methoxy-diphenyl-a.min to 3-oxy-4'-methoxy-N -nitroso-diphenylamine, rearrangement to 4-nitroso-3-oxy-4'-methoxy-diphenylamine, reduction and acetylation to 4-acetylamino-3-oxy-4'-methoxy-diphenylamine)
are dissolved in 150 parts by volume of alcohol and 25 parts by volume of 31% sodium hydroxide solution, heated to 50 ° C. and 20 parts by weight of diethyl sulfate are added at 50 to 55 ° C. over the course of 15 minutes and then to about 60 ° for a further 15 minutes C held. The clear solution thus obtained is diluted with the same amount of water, whereby the 4-acetylamino-3-ethoxy-4'-methoxy-diphenylamine separates out in crystalline form.
The product isolated as usual and purified by recrystallization is boiled for 3 hours with 75 parts by volume of alcohol and 25 parts by volume of 20% hydrochloric acid to saponify the acetyl group. The hydrochloric acid salt of 4-amino-3-ethoxy-4'-methoxy-diphenyl.amine crystallizes from the solution obtained in this way on cooling. The free base crystallizes from cyclohexane in colorless flakes with a melting point of 74 to 75 ° C. (uncorrected).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE175234X | 1932-08-31 | ||
| CH170086T | 1933-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH175234A true CH175234A (en) | 1935-02-15 |
Family
ID=25718840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH175234D CH175234A (en) | 1932-08-31 | 1933-07-29 | Process for the preparation of 4-amino-3-ethoxy-4'-methoxy-diphenylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH175234A (en) |
-
1933
- 1933-07-29 CH CH175234D patent/CH175234A/en unknown
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