DE859147C - Process for the preparation of 1-p-halophenyl-2-acylamino-1, 3-dioxypropanes - Google Patents

Process for the preparation of 1-p-halophenyl-2-acylamino-1, 3-dioxypropanes

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Publication number
DE859147C
DE859147C DEE2051A DEE0002051A DE859147C DE 859147 C DE859147 C DE 859147C DE E2051 A DEE2051 A DE E2051A DE E0002051 A DEE0002051 A DE E0002051A DE 859147 C DE859147 C DE 859147C
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DE
Germany
Prior art keywords
dioxypropanes
halophenyl
acylamino
preparation
formula
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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
DEE2051A
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German (de)
Inventor
Gustav Dr Ehrhart
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.)
Hoechst AG
Original Assignee
Hoechst AG
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Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEE2051A priority Critical patent/DE859147C/en
Application granted granted Critical
Publication of DE859147C publication Critical patent/DE859147C/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

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

Description

Verfahren zur Herstellung von 1-p-Halogenphenyl-2-acylamino-1, 3-dioxypropanen Bekanntlich zeigt das x-p-Nitrophenyl-2-dichloracetamino-x, 3-dioxvpropan der folgenden Formel ein Stoffwechselprodukt aus Streptomyces venezuelae (J. Bact. 66, 467 [19481; amerikanische Patenschrift 2 483 871), hervorragende antibiotische Eigenschaften. Es ist unter dem Namen Chloramphenicol oder Chloromycetin bekanntgeworden.Process for the preparation of 1-p-halophenyl-2-acylamino-1,3-dioxypropanes It is known that xp-nitrophenyl-2-dichloroacetamino-x shows 3-dioxvpropane of the following formula a metabolic product from Streptomyces venezuelae (J. Bact. 66, 467 [19481; American patent specification 2,483,871), excellent antibiotic properties. It has come to be known as chloramphenicol or chloromycetin.

Es wurde nun gefunden, daB man durch Überführung von Halogenphenylserinestern der Formel worin X Halogen und Y einen Alkylrest bedeutet, nach an sich bekannten Methoden, vorzugsweise mit Lithium-Aluminium-Hydrid, in die entsprechenden Halogenphenyl-amino-propandiole der Formel und ihre Acylierung, z. B. mittels Dichloracetylchlorid oder Dichloressigester, zu den entsprechenden Amiden der Formel wobei R einen Säurerest bedeutet, gelangt, die ganz hervorragende antibiotische Eigenschaften aufweisen.It has now been found that by converting halophenylserine esters of the formula in which X is halogen and Y is an alkyl radical, according to methods known per se, preferably with lithium-aluminum hydride, into the corresponding halophenylamino-propanediols of the formula and their acylation, e.g. B. by means of dichloroacetyl chloride or dichloroacetic ester, to the corresponding amides of the formula where R denotes an acid residue, which have excellent antibiotic properties.

Beispiel 8 g p-Chlorphenylserinäthylester, erhalten durch Verestern von p-Chlorphenylserin mit Äthanol und Salzsäure, werden in 3oo ccm abs. Äther gelöst und zu einer Lösung von 4. bis 5 g Aluminium-Lithium-Hydrid in Äther unter Rühren zugetropft. Dann wird unter guter Kühlung Wasser zugetropft. Durch Extraktion mit Äther und Benzol werden 6 bis 7 g i-p-Chlorphenyl-2-amino-i, 3-dioxypropan vom F. = 123 bis 124' erhalten. 7,5 g dieser Verbindung und 6,5 g Dichloressigester werden in 5o ccm Äther so lange unter Rückfluß gekocht, bis kein freies Amin mehr nachweisbar ist (mehrere Stunden). Die Ätherlösung wird mit verdünnter Salzsäure durchgeschüttelt und der Ätherauszug vom Äther befreit. Der erstarrte Rückstand wird in wenig Methanol gelöst und mit Wasser bis fast zur Trübung versetzt. Es kristallisieren 7,5 g i-p-Chlorphenyl-z-dichloracetylamino-i, 3-dioxypropan vom F. = i2o bis 121' aus.Example 8 g of p-chlorophenylserine ethyl ester, obtained by esterification of p-chlorophenylserine with ethanol and hydrochloric acid are in 3oo ccm abs. Ether dissolved and to a solution of 4 to 5 g of aluminum-lithium hydride in ether with stirring added dropwise. Then water is added dropwise with good cooling. By extraction with Ether and benzene are 6 to 7 g of i-p-chlorophenyl-2-amino-i, 3-dioxypropane from F. = 123 to 124 'obtained. 7.5 g of this compound and 6.5 g of dichloroacetate are used refluxed in 50 cc of ether until no free amine can be detected is (several hours). The ether solution is shaken with dilute hydrochloric acid and the ether extract freed from the ether. The solidified residue is dissolved in a little methanol dissolved and mixed with water until almost cloudy. 7.5 g of i-p-chlorophenyl-z-dichloroacetylamino-i crystallize, 3-dioxypropane from F. = i2o to 121 '.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von i-p-Halogenphenyl-2-acylamino-i, 3-dioxypropanen, dadurch gekennzeichnet, daß man Halogenphenylserinester der Formel wobei K Halogen und Y einen Alkylrest bedeuten, nach an sich bekannten Methoden, vorzugsweise mit Lithium-Aluminium-Hydrid, in die entsprech enden Halo,enphenyl-amino-propandiole der Formel überführt und diese mit Acylierungsmitteln, wie Dichloracetylchlorid oder Dichloressigester, in die entsprechenden Amide verwandelt.PATENT CLAIM: Process for the preparation of ip-halophenyl-2-acylamino-i, 3-dioxypropanes, characterized in that halophenylserine esters of the formula where K is halogen and Y is an alkyl radical, according to methods known per se, preferably with lithium-aluminum hydride, into the corresponding halo, enphenylamino-propanediols of the formula and these converted into the corresponding amides with acylating agents such as dichloroacetyl chloride or dichloroacetic ester.
DEE2051A 1950-09-05 1950-09-05 Process for the preparation of 1-p-halophenyl-2-acylamino-1, 3-dioxypropanes Expired DE859147C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEE2051A DE859147C (en) 1950-09-05 1950-09-05 Process for the preparation of 1-p-halophenyl-2-acylamino-1, 3-dioxypropanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEE2051A DE859147C (en) 1950-09-05 1950-09-05 Process for the preparation of 1-p-halophenyl-2-acylamino-1, 3-dioxypropanes

Publications (1)

Publication Number Publication Date
DE859147C true DE859147C (en) 1952-12-11

Family

ID=7065489

Family Applications (1)

Application Number Title Priority Date Filing Date
DEE2051A Expired DE859147C (en) 1950-09-05 1950-09-05 Process for the preparation of 1-p-halophenyl-2-acylamino-1, 3-dioxypropanes

Country Status (1)

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DE (1) DE859147C (en)

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