DE664048C - Process for the preparation of clusters of phenylenediamines - Google Patents

Process for the preparation of clusters of phenylenediamines

Info

Publication number
DE664048C
DE664048C DEI54603D DEI0054603D DE664048C DE 664048 C DE664048 C DE 664048C DE I54603 D DEI54603 D DE I54603D DE I0054603 D DEI0054603 D DE I0054603D DE 664048 C DE664048 C DE 664048C
Authority
DE
Germany
Prior art keywords
reduction
phenylenediamines
weight
clusters
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEI54603D
Other languages
German (de)
Inventor
Dr Richard Kuhn
Dr Rudolf Stroebele
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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
Priority to DEI54603D priority Critical patent/DE664048C/en
Application granted granted Critical
Publication of DE664048C publication Critical patent/DE664048C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Durch das Patent 642148 wird ein Verfahren zur Darstellung von Abkömmlingen von Phenylendiaminen geschützt. Das Verfahren besteht darin, daß man Zucker auf 5 o-Nitroaniline einwirken läßt und die Kondensationispro'dukte reduziert. Bei der Reduktion durch katalytisch erregten Wasserstoff erhält man je nach den Bedingungen, z. B. je nach der Art des Katalysators und der Katalysatormenge, dem angewandten Druck und der angewandten Temperatur Phenylendiaminderivate, in denen außer der Nitrogruppe auch, die glukosidartige Bindung des Zuckerrestes an die Aminogruppe mehr oder weniger reduziert ist. Aus den Phenylendiaminverbindungen mit glukosidischer Bindung des Zuckerrestes läßt sich der Zuckerrest durch Säuren leicht .wieder abspalten. Dagegen sind die Reduktionsprodukte, in denen auch die glukosidische Bindung des Zuckerrestes an die Aminogruppe hydriert wurde, gegenüber verdünnten Säuren beständig.Patent 642148 provides a method protected for the representation of derivatives of phenylenediamines. The procedure consists in allowing sugar to act on 5 o-nitroanilines and the condensation products reduced. In the case of reduction by catalytically excited hydrogen, depending on the conditions, one obtains z. B. depending on the type of catalyst and the amount of catalyst, the pressure applied and the temperature used phenylenediamine derivatives in which, in addition to the nitro group also, the glucoside-like bond of the sugar residue to the amino group more or less is reduced. From the phenylenediamine compounds with a glucosidic bond The sugar residue can easily be split off again by acids. Against it are the reduction products, in which also the glucosidic bond of the sugar residue was hydrogenated to the amino group, resistant to dilute acids.

Es hat sich nun weiter gezeigt, daß die glukosidische Bindung des Zuckerrestes, an die Aminogruppe des Phenylendiamins bei der Reduktion praktisch unverändert bleibt, wenn man die Acylverbindungea der aus den Zukkern und den o-Nitroanilinen erhältlichen N-Glukoside in nicht saurem Medium einer gelinden Reduktion unterwirft. Katalytisch erregten Wasserstoff läßt man zweckmäßig in Gegenwart organischer Basen, wie z. B. Triäthylamin, auf die Acylverbindungen einwirken. Die Acylreste lassen sich durch milde Verseifungsmittel, z. B. alkoholische Ammoniaklösung, aus den Reduktionsprodukten abspalten.It has now also been shown that the glucosidic bond of the sugar residue to the amino group of the phenylenediamine remains practically unchanged during the reduction if the acyl compounds from the sugar nucleus and the o-nitroanilines available N-glucosides in a non-acidic medium subject to mild reduction. Catalytically excited hydrogen is expediently left in the presence of organic bases, such as. B. triethylamine act on the acyl compounds. The acyl residues can be removed by mild saponifying agents, e.g. B. alcoholic ammonia solution, from the reduction products split off.

Reduziert man z. B. das Triacetylderivat des i-(d-Ribosidoamino)-2-nitro-4, 5-dimethylbenzols in Essigesterlösung bei gewöhnlicher Temperatur mit Wasserstoff in Gegenwart von Platinoxyd und Triäthylamin, entsteht die entsprechende 2-Aminoverbindung. Dagegen wird das i-(d-Ribosidoamino)-2-nitro-4, 5-dimethylbenzol in Lösung von 850/oigem Alkohol bei 25 atü und bei gewöhnlicher Temperatur · in Gegenwart von etwa 0,12 Gewichtsteilen Palladium innerhalb von 7 Stunden zum i-(d-Ribitylamino)-2-amino-4,5-dimethyl benzol vollständig hydriert.If you reduce z. B. the triacetyl derivative of i- (d-ribosidoamino) -2-nitro-4,5-dimethylbenzene in ethyl acetate solution at ordinary temperature with hydrogen in the presence of Platinum oxide and triethylamine, the corresponding 2-amino compound is formed. Against it will the i- (d-ribosidoamino) -2-nitro-4,5-dimethylbenzene in a solution of 850% alcohol 25 atm and at ordinary temperature · in the presence of about 0.12 parts by weight Palladium to i- (d-ribitylamino) -2-amino-4,5-dimethylbenzene within 7 hours fully hydrogenated.

Behandelt man i-(Triacetyl-l-arabinosidoamino)-2-nitro-4, 5-dimethylbenzol in etwaIf i- (triacetyl-l-arabinosidoamino) -2-nitro-4 is treated, 5-dimethylbenzene roughly

"■') Von dem Patentsucher sind als die Erfinder angegeben worden:"■ ') The patent seeker stated that the inventors were: Dr. Richard Kuhn in Heidelberg und Dr. Rudolf Ströbele in Schkopau b. Merseburg.Dr. Richard Kuhn in Heidelberg and Dr. Rudolf Ströbele in Schkopau b. Merseburg.

(564048(564048

2O Gewichtsteilen Essigsäuremethylesier in Gegenwart von ο, 15 Gewichtsteilen Platinoxyd und 1,5 Gewichtsteilen Triäthylafnin mit Wasserstoff bei 20° und ratü, erfolgt Reduktion, zur entsprechenden 2-Aminoverbindung ii
halb etwa 1 Stunde.20 parts by weight of acetic acid methyl ester in the presence of ο, 15 parts by weight of platinum oxide and 1.5 parts by weight of triethylafnine with hydrogen at 20 ° and ratü, reduction takes place to give the corresponding 2-amino compound ii
half about 1 hour.

Löst man 1 Gewichtsteil i-(Triaoet
d-ribosidoamino)-2-nitro-4, 5-dimethylbenzol in 200 Gewichtsteilen Alkohol, versetzt mit einem Überschuß von Titantrihydroxyd in 40 Gewichtsteilen Wasser und erwärmt 1 Stunde lang auf 40° und filtriert, enthält die Lösung das gebildete i-(Triacetyl-d-ribosidoamino)-2-amino-4, 5-dimethylbenzol. Es kann gegebenenfalls nach Entfernen des Lösemittels unmittelbar weiterverarbeitet werden.If you dissolve 1 part by weight of i- (Triaoet
d-ribosidoamino) -2-nitro-4,5-dimethylbenzene in 200 parts by weight of alcohol, treated with an excess of titanium trihydroxide in 40 parts by weight of water and heated for 1 hour at 40 ° and filtered, the solution contains the i- (triacetyl- d-ribosidoamino) -2-amino-4,5-dimethylbenzene. If necessary, it can be further processed immediately after the solvent has been removed.

Claims (2)

Patentansprüche:Patent claims: 1. Weitere Ausbildung des durch Patent 642148 geschützten Verfahrens zur ,Darstellung von Abkömmlingen von Phe-•nyJendiaminen, dadurch gekennzeichnet, daß man die Kondensationsprodukte der •'Zucker mit o-Nitroanüinen in Form ihrer Acylverbindungen in nicht saurem Medium einer milden Reduktion unterwirft und aus den Reduktionsprodukten gegebenenfalls die Acylgruppen abspaltet.1. Further development of the process protected by patent 642148 , Representation of descendants of Phe- • nyJendiaminen, characterized in that the condensation products of • 'Sugars with o-nitroanuins in the form of their acyl compounds in a non-acidic medium subjected to a mild reduction and optionally from the reduction products splits off the acyl groups. 2. Ausführungsform des Verfahrens nach Anspruch 1, ,dadurch gekennzeichnet, daß man die Reduktion in Gegenwart einer organischen Base mittels katalytisch erregtem Wasserstoff bewirkt.2. Embodiment of the method according to claim 1, characterized in that the reduction in the presence of an organic base by means of catalytically excited Hydrogen causes.
DEI54603D 1936-02-01 1936-02-01 Process for the preparation of clusters of phenylenediamines Expired DE664048C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI54603D DE664048C (en) 1936-02-01 1936-02-01 Process for the preparation of clusters of phenylenediamines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI54603D DE664048C (en) 1936-02-01 1936-02-01 Process for the preparation of clusters of phenylenediamines

Publications (1)

Publication Number Publication Date
DE664048C true DE664048C (en) 1938-08-19

Family

ID=7193913

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI54603D Expired DE664048C (en) 1936-02-01 1936-02-01 Process for the preparation of clusters of phenylenediamines

Country Status (1)

Country Link
DE (1) DE664048C (en)

Similar Documents

Publication Publication Date Title
DE1793759C3 (en) H3 ', 5'-dihydroxyphenyl) -2- (imethylcyclobutylamino) ethanol and its physiologically acceptable acid addition salts, processes for their preparation and pharmaceuticals containing them
DE1620694C3 (en) Process for the preparation of 5-methyl-7-diethylamino-s-triazolo [1,5-a] pyrimidine and its salts with acids
DE1569807B2 (en) Oxyethylated nitro-p-phenylenediamine dyes, their production and colorants made from them
DE664048C (en) Process for the preparation of clusters of phenylenediamines
DE1545645A1 (en) Process for the preparation of disubstituted adenosine derivatives
DE1056139B (en) Process for the preparation of alpha-amino-beta-oxy-carboxylic acid anilides
DE1913184A1 (en) 4,5,6,7-Tetrahydrobenzimidazoles, process for their preparation and their use as corrosion inhibitors and anti-aging agents
DE1593848A1 (en) Process for the preparation of amino acids and peptides and their derivatives
DE1044084B (en) Process for the preparation of new piperidine compounds
DE1084718B (en) Process for the manufacture of secosteroids
DE396508C (en) Process for the preparation of a reduction product of anhydrolupinine
DE944731C (en) Process for the manufacture of p-aminobenzenesulfonamide capsules
DE962333C (en) Process for the preparation of cyclohexanone oxime
DE890345C (en) Process for the preparation of hydrogenated formylpteroic acids
DE542801C (en) Process for the production of real Kuepen dyes
DE2134289C3 (en) Pyrazole derivatives
DE899355C (en) Process for the preparation of pteroic acids
DE1804392A1 (en) 9-0-Kalamycin derivatives and process for their preparation
DE595188C (en) Process for the preparation of 4-aminodiphenylamine derivatives
DE1022574B (en) Process for the preparation of 1-amino-1-deoxy-2-ketoses and their salts
DE973048C (en) Process for the preparation of substituted morpholines suitable as medicinal products
DE968485C (en) Process for the production of guanidides of organic sulfonic acids
DE839354C (en) Process for the preparation of 3-oxy-í¸-12-alkoxycholenic acid alkyl esters from the corresponding 12-keto compounds
DE1493579C (en) Process for the production of new pharmaceutically valuable compounds
DE1180750B (en) Process for the production of chimney acid and its derivatives