DE607381C - Process for the preparation of oxycarboxylic acid arylamides - Google Patents

Process for the preparation of oxycarboxylic acid arylamides

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Publication number
DE607381C
DE607381C DEI45455D DEI0045455D DE607381C DE 607381 C DE607381 C DE 607381C DE I45455 D DEI45455 D DE I45455D DE I0045455 D DEI0045455 D DE I0045455D DE 607381 C DE607381 C DE 607381C
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Germany
Prior art keywords
amino
chlorobenzene
preparation
arylamides
oxycarboxylic acid
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DEI45455D
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German (de)
Inventor
Dr Friedrich Muth
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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Priority to DEI45455D priority Critical patent/DE607381C/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Oxycarbonsäurearylamiden Es wurde gefunden, daß man wertvolle Zwischenprodukte für die Herstellung von Farbstoffen erhält, wenn man die durch Carbonisierung von 2- oder 3-Oxyverbindungen von Ringsystemen der allgemeinen Formel worin X O, S, SO, bedeuten kann, erhältlichen o-Oxycarbonsäuren in ihre Arylamide überführt.Process for the preparation of oxycarboxylic arylamides It has been found that valuable intermediates for the preparation of dyes are obtained if the carbonization of 2- or 3-oxy compounds of ring systems of the general formula is used where XO, S, SO, can mean, converts available o-oxycarboxylic acids into their arylamides.

Die als Ausgangsprodukte verwendeten Oxycarbonsäuren werden beispielsweise nach dem Verfahren des Patents 593 5o6 erhalten.The oxycarboxylic acids used as starting materials are for example obtained by the method of patent 593 5o6.

Die Überführung dieser Carbonsäuren in ihre Arylamide erfolgt nach bekannten Methoden, z. B. durch Umsetzung der Carbonsäuren in Form ihrer Säurechloride oder Ester mit aromatischen oder heterocyclischen Aminen, wie Aminen der Benzol-, Naphthalin- und Carbazolreihe, oder durch Umsetzung der freien Carbonsäuren mit Arylestern der Isocyansäure. Aus dem bekannten Verfahren zur Herstellung von Arylamiden der 2, 3-Oxynaphthoesäure bzw. der 2, 3-Oxyanthracencarbonsäure konnte nicht geschlossen werden, daB..die Reaktion bei heterocyclischen Ringsystemen, die sich bekanntlich in ihrer Reaktionsfähigkeit anders verhalten als einfache Kohlenwasserstoffe, in der angegebenen Richtung verläuft. Beispiel i 19,2 g 3-Oxydiphenylenoxyd-o-carbonsäure und 15,5 g i Amino-2-methoxy-q.-chlorbenzol werden in 500 ccm Toluol gelöst. Bei 6o bis 65° C läßt man unter Rühren langsam 6 g Phosphortrichlorid eintropfen, erwärmt zum Sieden und hält unter Rühren etwa 8 Stunden bei dieser Temperatur. Dann macht man mit Natriumcarbonat alkalisch, bläst mit Wasserdampf das Toluol und überschüssiges Amin ab, saugt ab und wäscht mit Wasser aus. Der Rückstand wind in viel Wasser unter Zusatz von Natronlauge gelöst und aus der stark gelb gefärbten Lösung das Arylid durch Ansäuern mit verdünnter Salzsäure ausgefällt. Aus Pyridin kristallisiert es in gelb gefärbten, zu Sternchen vereinigten Nädelchen vom F. 255° C.These carboxylic acids are converted into their arylamides by known methods, e.g. B. by reacting the carboxylic acids in the form of their acid chlorides or esters with aromatic or heterocyclic amines, such as amines of the benzene, naphthalene and carbazole series, or by reacting the free carboxylic acids with aryl esters of isocyanic acid. From the known process for the preparation of arylamides of 2,3-oxynaphthoic acid or 2,3-oxyanthracenecarboxylic acid, it could not be concluded that the reaction in heterocyclic ring systems, which are known to behave differently in their reactivity than simple hydrocarbons in the specified direction. Example i 19.2 g of 3-oxydiphenylene oxide-o-carboxylic acid and 15.5 g of amino-2-methoxy-q.-chlorobenzene are dissolved in 500 cc of toluene. At 60 ° to 65 ° C., 6 g of phosphorus trichloride are slowly added dropwise with stirring, the mixture is heated to the boil and kept at this temperature for about 8 hours with stirring. Then make alkaline with sodium carbonate, blow off the toluene and excess amine with steam, suction off and wash out with water. The residue is dissolved in a lot of water with the addition of sodium hydroxide solution and the arylide is precipitated from the strongly yellow-colored solution by acidification with dilute hydrochloric acid. It crystallizes from pyridine in yellow-colored needles that are combined to form asterisks with a temperature of 255 ° C.

Das Arylid aus der isomeren 2-Oxydiphenylenoxyd-o-carbonsäure und i-Amino-2-inethoxy-4-chlorbenzol schmilzt bei 215° C.The arylide from the isomeric 2-oxydiphenylene oxide-o-carboxylic acid and i-Amino-2-ynethoxy-4-chlorobenzene melts at 215 ° C.

In entsprechender Weise erhält man aus 3 -Oxydiphenylenoxyd-o-carbonsäure und Anilin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ein Arylid vom F. 289° 2-Toluidin .......... . ....................... - - - - 263' 2-Anisidin ........................... . ...... - - - - 2Z3° 4-Anisidin .................................. - - - - 286° 2-Phenetidin ................... . ............ - - - - 200° Z-Chloranilin..................... ............ - - - - 2630 4-Chloranilin................................ - - - - 335° 3-Nitranilin................................. - - - - 297° i-Amino-2,5-dimethylbenzol.................. - - - - 2I4 i-Amino-3, 5-dimethylbenzol . . . . . . . . . . . . . . . . . . - - - - 24I' iAmino-Z-methyl-4-methoXybenzol...... ...... - - - - Z43° i-Amino-3-methyl-4-methoxybenzol..... ....... - - - - Z53° i-Amino-2-methyl-4-chlorbenzol ............... - - - - 299, i-Amino-2-methyl-5-chlorbenzol ............... - - - - 250' i-Amino-2, 4-dimethoxybenzol............. 28I00 i-Amino-2, 5-dimethoxybenzol................. - - - - Z17 i-Amino-2-methoxy-5-chlorbenzol.............. - - - - Z37° i-Amino-2-sulfodiäthylamino-4-chlorbenzol...... - - - - 140° i Amino-Z, 4-dimethoxy-5-chlorbenzol. . . ....... - - - - Z85° i-Amino-2, 5-dimetlloxy-4-chlorbenzol . . . . . . . . . : - - - - - 2850 a-Naphthylamin............................. - - - - Z95° ` Beispiel: Das in analoger Weiseatxs 3-Oxydiphenylensulfid-o-carbonsäure und i Amino-2-inethoxy-4-elilorbenzol hergestellte Arylid, das sich in Wasser oder Alkohol unter Zusatz von Natroillauge mit intensiv gelber Farbe und kräftiger grünstichiger Fluoreszenz löst, schmilzt bei 234° C.In a corresponding way one obtains from 3-Oxydiphenylenoxyd-o-carboxylic acid and Aniline. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . an arylid with a temperature of 289 ° 2-toluidine ........... ....................... - - - - 263 ' 2-anisidine ............................ ...... - - - - 2Z3 ° 4-anisidine .................................. - - - - 286 ° 2-phenetidine .................... ............ - - - - 200 ° Z-chloroaniline. ..................... ........... - - - - 2630 4-chloroaniline ................................ - - - - 335 ° 3-nitroaniline ................................. - - - - 297 ° i-Amino-2,5-dimethylbenzene .................. - - - - 2I4 i-amino-3,5-dimethylbenzene. . . . . . . . . . . . . . . . . . - - - - 24I ' iAmino-Z-methyl-4-methoXybenzene ...... ...... - - - - Z43 ° i-Amino-3-methyl-4-methoxybenzene ...... ...... - - - - Z53 ° i-Amino-2-methyl-4-chlorobenzene ............... - - - - 299, i-Amino-2-methyl-5-chlorobenzene ............... - - - - 250 ' i-Amino-2,4 -dimethoxybenzene ............. 28I00 i-Amino- 2,5-dimethoxybenzene ................. - - - - Z17 i-Amino-2-methoxy-5-chlorobenzene .............. - - - - Z37 ° i-Amino-2-sulfodiethylamino-4-chlorobenzene ...... - - - - 140 ° i Amino-Z, 4-dimethoxy-5-chlorobenzene. . . ....... - - - - Z85 ° i-amino-2,5-dimetlloxy-4-chlorobenzene. . . . . . . . . : - - - - - 2850 a-Naphthylamine ............................. - - - - Z95 ° ` Example: The arylide produced in an analogous manner atxs 3-oxydiphenylene sulfide-o-carboxylic acid and i-amino-2-ynethoxy-4-elilobenzene, which dissolves in water or alcohol with the addition of sodium hydroxide solution with an intense yellow color and strong greenish fluorescence, melts at 234 ° C.

Das Arylid aus 3-Oxydiphenylensulfono-carbonsäure und i-Amino-2-methoxy-4-chlorbenzol ist ein gelb gefärbter Körper vom F. über 300° C.The arylide from 3-oxydiphenylenesulfonocarboxylic acid and i-amino-2-methoxy-4-chlorobenzene is a yellow colored body from the F. over 300 ° C.

In entsprechender Weise erhält man aus 3-Oxydiphenylensulfid-o-carbo-nsäure und Anilin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...... ein Arylid vom F. 289' 2 Toluidin ...... . ................ . .......... - - - - 2070 4 Toluidin .................................. - - - - 2950 2-Anisidin .................................. - - - - 1950 4-Anisidin .................................. - - - - 255ö 2-Phenetidin ................................ - - - - 205 4-Phenetidin ......... , .................... - - - - 265ö 4-Chloranilin................ ................. - - - - 3050 2-Nitranilin............................. .... - - - - 233 3-Nitranilin..........:...................... - - - - 302, 0 i-Amino-Z, 5-dimethylbenzol . . . . . . . . . . . . . . . . . - igo i-Amino-2-methyl-4-methoxybenzol............. - - - - 2440 i-Amino-3-methyl-4-methoxybenzol............ - - - - 2450 z-Amino-2-methyl 4-chlorbenzol . . . . . . . . . . . . . . . - - - - 2680 i Amino-2-methyl-5-chlorbenzol............... - - - - 2330 i-Amino-a, 4-dimethoxybenzol................. - - - - 26o0 0 i-Amino-2, 5-dimethoxybenzol................. - - - 203 o- i-Amino-2-methoxy-5-chlorbenzol.............. - - - - 250 i-Amino-3,4-dichlorbenzol.................... - - - - 2880 i-Amino-2,4-dimethoxy-5-chlorbenzol.......... - - - - 2570 i-Amino-2,5-dimethoxy-4-chlorbenzol.......... - - - - 2330 2-Amino-6-äthoxybenzothiazol ................ - - - - Z700 a-Naphthylamin............................. - - - - 238' i-Aminocarbazol............................. - _ - - 3000 Beispiel 3 2¢,4 g 3 - Ox3-diphenylensulfid -;o - carbonsäure und 15 g Dianisidin werden in 1j2 1 Toluol suspendiert. Bei 6o bis 70' C tropft man 7 g Phosphortrichlorid zu, erwärmt dann langsam zum Sieden und kocht unter gutem Rühren, bis die graue Anschläm:mung in die gelbe des Arylids übergegangen ist. Dann wird sodaalkalisch das Toluol abgeblasen und der gelbe Rückstand mit warmer, verdünnter Salzsäure verrieben, abgesaugt und säurefrei gewaschen. Man erhält ein gelb gefärbtes Produkt vom F. 336'C.In a corresponding way one obtains from 3-oxydiphenylene sulfide-o-carbonic acid and Aniline. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...... an arylid of F. 289 ' 2 toluidine ....... ................. .......... - - - - 2070 4 toluidine .................................. - - - - 2950 2-anisidine .................................. - - - - 1950 4-anisidine .................................. - - - - 255ö 2-phenetidine ................................ - - - - 205 4-phenetidine ........., .................... - - - - 265ö 4-chloroaniline ................. ................ - - - - 3050 2-nitroaniline ............................. .... - - - - 233 3-nitroaniline ..........: ...................... - - - - 302, 0 i-amino-Z, 5-dimethylbenzene. . . . . . . . . . . . . . . . . - igo i-Amino-2-methyl-4-methoxybenzene ............. - - - - 2440 i-Amino-3-methyl-4-methoxybenzene ............ - - - - 2450 z-amino-2-methyl-4-chlorobenzene. . . . . . . . . . . . . . . - - - - 2680 i Amino-2-methyl-5-chlorobenzene ............... - - - - 2330 i-Amino-a, 4-dimethoxybenzene ................. - - - - 26o0 0 i-Amino-2,5-dimethoxybenzene ................. - - - 203 O- i-Amino-2-methoxy-5-chlorobenzene .............. - - - - 250 i-Amino-3,4-dichlorobenzene .................... - - - - 2880 i-Amino-2,4-dimethoxy-5-chlorobenzene .......... - - - - 2570 i-Amino-2,5-dimethoxy-4-chlorobenzene .......... - - - - 2330 2-Amino-6-ethoxybenzothiazole ................ - - - - Z700 a-naphthylamine ............................. - - - - 238 ' i-aminocarbazole ............................. - _ - - 3000 Example 3 2 ¢, 4 g of 3 - Ox3-diphenylene - o - carboxylic acid and 1 5 g dianisidine are suspended in 1 1J2 toluene. At 60 to 70 ° C., 7 g of phosphorus trichloride are added dropwise, then slowly heated to the boil and boiled with thorough stirring until the gray slurry has changed into the yellow of the arylide. The toluene is then blown off using alkaline soda and the yellow residue is triturated with warm, dilute hydrochloric acid, filtered off with suction and washed free of acid. A yellow-colored product with a melting point of 336'C is obtained.

Claims (1)

PATL.NTANSPRUCFI Verfahren zur Herstellung von Oxycarbonsäurearylamiden, dadurch gekennzeichnet, daß man die durch Carbonisierung von a- oder 3-Oxvverbindungen von Ringsystemen der allgemeinen Formel worin X O, S, S 02 bedeutet, erhältlichen o-Oxvcarbonsäuren nach bekannten Verfahren in ihre Arylamide überführt.PATL.NTANSPRUCFI Process for the preparation of oxycarboxylic acid arylamides, characterized in that the carbonization of α- or 3-Oxvverbindungen of ring systems of the general formula where X is O, S, S 02, obtainable o-oxycarboxylic acids are converted into their arylamides by known processes.
DEI45455D 1932-10-06 1932-10-06 Process for the preparation of oxycarboxylic acid arylamides Expired DE607381C (en)

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DEI45455D DE607381C (en) 1932-10-06 1932-10-06 Process for the preparation of oxycarboxylic acid arylamides

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