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.

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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
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH175234A publication Critical patent/CH175234A/en

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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)

PATENTANSPUUC!aVerfahren zur Darstellung des 4-Amino- 3-äthogy-4'-methogy-diphenylamins, dadurch gekennzeichnet, dass man 4-Acetylamino-3- oxy - 4'- methoxy - diphenylamin mit einem äthylierenden Mittel behandelt und sodann das erhaltene 4-Acetylamino-3-äthogy-4'-me- thoxy-diphenylamin durch Verseifen in die freie Aminoverbindung überführt. A method for the preparation of 4-amino-3-ethogy-4'-methogy-diphenylamine, characterized in that 4-acetylamino-3-oxy-4'-methoxy-diphenylamine is treated with an ethylating agent and then the 4 Acetylamino-3-ethogy-4'-methoxy-diphenylamine converted into the free amino compound by saponification. Die so erhaltene Verbindung kristallisiert aus Cyclohexan in farblosen Blättchen vom Schmelzpunkt 74 bis 75 C. <B>D</B> UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als äthylierendes Mittel Diäthylsulfat verwendet. The compound obtained in this way crystallizes from cyclohexane in colorless flakes with a melting point of 74 to 75 C. SUBClaim: Process according to patent claim, characterized in that diethyl sulfate is used as the ethylating agent.
CH175234D 1932-08-31 1933-07-29 Process for the preparation of 4-amino-3-ethoxy-4'-methoxy-diphenylamine. CH175234A (en)

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)

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