DE824208C - Process for the preparation of N- (ß-chloroethyl) -diarylamines - Google Patents

Process for the preparation of N- (ß-chloroethyl) -diarylamines

Info

Publication number
DE824208C
DE824208C DEP42637A DEP0042637A DE824208C DE 824208 C DE824208 C DE 824208C DE P42637 A DEP42637 A DE P42637A DE P0042637 A DEP0042637 A DE P0042637A DE 824208 C DE824208 C DE 824208C
Authority
DE
Germany
Prior art keywords
chloroethyl
diarylamines
thionyl chloride
preparation
solvents
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
DEP42637A
Other languages
German (de)
Inventor
Dr Erich Rabald
Dr Hermann Dimroth
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.)
Roche Diagnostics GmbH
CF Boehringer und Soehne GmbH
Original Assignee
Boehringer Mannheim GmbH
CF Boehringer und Soehne GmbH
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 Boehringer Mannheim GmbH, CF Boehringer und Soehne GmbH filed Critical Boehringer Mannheim GmbH
Priority to DEP42637A priority Critical patent/DE824208C/en
Application granted granted Critical
Publication of DE824208C publication Critical patent/DE824208C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups

Landscapes

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

Description

Verfahren zur Herstellung von N-(ß-Chloräthyl)-diarylaminen N-(ß-Chloräthyl)-diarylamine, welche als solche oder als Zwischenprodukte bei der Herstellung von Arzneimitteln eine große Rolle spielen, lassen sich am vorteilhaftesten durch Umsetzung der entsprechenden ß-Diarylamino-äthanole mit Thionylchlorid, hauptsächlich in benzolischer Lösung, darstellen (vgl. Bull. Soc. chim. France, 5, i, too6).Process for the production of N- (ß-chloroethyl) -diarylamines N- (ß-chloroethyl) -diarylamines, which as such or as intermediates in the manufacture of pharmaceuticals Play a big role can be most beneficial by implementing the appropriate ß-Diarylamino-ethanols with thionyl chloride, mainly in benzene solution, (cf. Bull. Soc. chim. France, 5, i, too6).

Es wurde nun gefunden, daß diese Reaktion in besonders glatter Weise und mit fast quantitativer Ausbeute verläuft, wenn man sie in Abwesenheit von Lösungsmitteln durchführt. Darüber hinaus wird durch das erfindungsgemäße Verfahren eine große Verbilligung bei der Herstellung dieser wichtigen Verbindungen dadurch erbracht, daß man mühelos und vollständig das eingesetzte Thionylchlorid wiedergewinnen kann, während eine Regenerierung desselben bei Anwesenheit von Lösungsmitteln nur schwierig und unter großen Verlusten möglich ist. Man kann also ohne weiteres mit einem großen Überschuß an Thionylchlorid arbeiten, was für den Verlauf der Reaktion an sich günstig ist. Die Verfahrensprodukte fallen nach dem Abdestillieren des überschüssigen Thionylchlorids sogleich in großer Reinheit an. Beispiel In 6oo g Thionylchlorid werden roo g N-ß-Oxyäthyldibenzylamin oder 115 g seines Chlorhydrats so rasch eingetragen, daß das Thionylchlorid dauernd im Sieden bleibt. Man läßt dann noch kurze Zeit kochen und destilliert das Thionylchlorid im Vakuum ab. Man erhält einen rein weißen, festen Rückstand, der für die weitere Ver-Nvendung direkt eingesetzt werden kann. Gegebenenfalls löst man das Produkt zur weiteren Reinigung in etwa 1 1 Wasser, behandelt kurz mit Tierkohle, versetzt das Filtrat mit 1o ccm konzentrierter Salzsäure und saugt nach ad Stunden ab. Man erhält 115 g N-ß-Chloräthyl-dibenzylamin-hydrochlorid (-94% der Theorie) ; Schmp. 180 bis i81°.It has now been found that this reaction works in a particularly smooth manner and proceeds with almost quantitative yield if you use them in the absence of solvents performs. In addition, the method according to the invention provides a large Reduction in the production of these important connections brought about by that you can easily and completely recover the thionyl chloride used, while regeneration of the same is difficult in the presence of solvents and is possible with great losses. So you can easily deal with a big one Excess thionyl chloride work, which is favorable for the course of the reaction is. The products of the process fall after the excess thionyl chloride has been distilled off at once in great purity. EXAMPLE In 600 g of thionyl chloride, roo g of N-ß-oxyethyldibenzylamine are added or 115 g of its chlorohydrate entered so quickly that the thionyl chloride continuously remains in the boil. The mixture is then left to boil for a short time and the thionyl chloride is distilled off in a vacuum. A pure white, solid residue is obtained, which for the further Usage can be used directly. If necessary, the product is dissolved for further cleaning in about 1 liter of water, treated briefly with animal charcoal, added the filtrate with 10 ccm concentrated hydrochloric acid and sucks off after ad hours. Man receives 115 g of N-ß-chloroethyl-dibenzylamine hydrochloride (-94% of theory); M.p. 180 to i81 °.

Claims (1)

PATENTnvsPi;i-cri: Verfahren zur Hersteliung von V-(/3-Chloräthyl)-diarylaininen durch Chlorierung der entsprechenden ß-Diarylamino-äthanole oder deren Salze mittels Thionylchlorid, dadurch gekennzeichnet, daß man die Umsetzung in Abwesenheit von Lösungsmitteln durchführt.PATENTnvsPi; i-cri: Process for the production of V - (/ 3-chloroethyl) -diarylainins by chlorination of the corresponding ß-diarylamino-ethanols or their salts by means of Thionyl chloride, characterized in that the reaction is carried out in the absence of Solvents performs.
DEP42637A 1949-05-14 1949-05-14 Process for the preparation of N- (ß-chloroethyl) -diarylamines Expired DE824208C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP42637A DE824208C (en) 1949-05-14 1949-05-14 Process for the preparation of N- (ß-chloroethyl) -diarylamines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP42637A DE824208C (en) 1949-05-14 1949-05-14 Process for the preparation of N- (ß-chloroethyl) -diarylamines

Publications (1)

Publication Number Publication Date
DE824208C true DE824208C (en) 1951-12-10

Family

ID=7378779

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP42637A Expired DE824208C (en) 1949-05-14 1949-05-14 Process for the preparation of N- (ß-chloroethyl) -diarylamines

Country Status (1)

Country Link
DE (1) DE824208C (en)

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