CH414641A - Process for the preparation of a new hydrazine derivative - Google Patents

Process for the preparation of a new hydrazine derivative

Info

Publication number
CH414641A
CH414641A CH1518664A CH1518664A CH414641A CH 414641 A CH414641 A CH 414641A CH 1518664 A CH1518664 A CH 1518664A CH 1518664 A CH1518664 A CH 1518664A CH 414641 A CH414641 A CH 414641A
Authority
CH
Switzerland
Prior art keywords
sulfamyl
methyl
oxo
acid amide
oxazolidone
Prior art date
Application number
CH1518664A
Other languages
German (de)
Inventor
Ernst Dr Jucker
Adolf Dr Lindenmann
Original Assignee
Sandoz 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
Priority claimed from CH1254760A external-priority patent/CH396905A/en
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH1518664A priority Critical patent/CH414641A/en
Priority claimed from CH654761A external-priority patent/CH418335A/en
Publication of CH414641A publication Critical patent/CH414641A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

       

  



  Verfahren zur Herstellung eines neuen   Hydrazin-Derivates   
Es wurde gefunden, dass man zum bisher unbekannten N-   [2'-Oxo-5'-methyloxazolidinyl-      (3')]-3-      sulfamyl-4-chlor-benzoesäureamid    der Formel I
EMI1.1     
 gelangt, indem man   3-Sulfamyl-4-chlor-benzoylchlorid    mit   3-Amino-5-methyl-oxazolidon- (2)    umsetzt.



   Beispiel   
N- [2'-Oxo-5'-methyl-oxazolidinyl- (3')]-
3-sulfamyl-4-chlor-benzoesäureamid   
Eine Lösung von 3,5 g   3-Amino-5-methyl-oxa-    zolidon- (2) und 3,0 g   Triäthylarmin    in 150 cm3 Chloroform wird unter Rühren bei 20-25  innert 30 Minuten mit 7,6 g   3-Sulfamyl-4-chlor-benzoyl-    chlorid versetzt. Darauf wird die Reaktionslösung während 60 Stunden bei Zimmertemperatur weitergerührt, wobei sich eine schmierige Masse   ausschei-    det. Man dampft im Vakuum zur Trockne ein, versetzt den   Eindampfrückstand    mit 300   cm8    Essigsäureäthylester und 150   cm    Wasser und schüttelt gut durch.

   Nach Trennung der Schichten wird die Essigsäureäthylesterlösung mit total 150 cm3 Wasser gewaschen und über Magnesiumsulfat getrocknet.



  Das Lösungsmittel wird im Vakuum abgedampft und der Rückstand über Aluminiumoxyd   chromatogra-      phiert    wobei das   N- [2'-Oxo-5'-methyl-oxazolidinyl-      (3]-3-sulfamyl-4-chlorbenzoesäureamid    mit einem Lösungsmittelgemisch von   Essigsaureäthylester/    Methanol (9 :   1)    eluiert wird. Nach Umkristallisieren aus   Chloroform/Methanol    (9 :   1)    schmilzt das   Sulfon-      amid-Derivat    bei   215-216 .     



   PATENTANSPRUCH
Verfahren zur Herstellung des bisher unbekannten   N-12'-Oxo-5'-methyl-oxazolidinyl-(3')]-3-sulfamyl-      4-chlor-benzoesäureamids    der Formel I
EMI1.2     
 dadurch gekennzeichnet, dass man 3-Sulfamyl-4-chlorbenzoylchlorid mit   3-Amino-5-methyl-oxazolidon- (2)    umsetzt. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the preparation of a new hydrazine derivative
It has been found that the previously unknown N- [2'-oxo-5'-methyloxazolidinyl- (3 ')] -3-sulfamyl-4-chloro-benzoic acid amide of the formula I
EMI1.1
 obtained by reacting 3-sulfamyl-4-chlorobenzoyl chloride with 3-amino-5-methyl-oxazolidone- (2).



   example
N- [2'-Oxo-5'-methyl-oxazolidinyl- (3 ')] -
3-sulfamyl-4-chloro-benzoic acid amide
A solution of 3.5 g of 3-amino-5-methyl-oxazolidone- (2) and 3.0 g of triethyl amine in 150 cm3 of chloroform is mixed with 7.6 g of 3-sulfamyl within 30 minutes while stirring at 20-25 -4-chloro-benzoyl chloride added. The reaction solution is then stirred for a further 60 hours at room temperature, a greasy mass separating out. It is evaporated to dryness in vacuo, the residue from evaporation is mixed with 300 cm8 of ethyl acetate and 150 cm of water and shaken well.

   After separating the layers, the ethyl acetate solution is washed with a total of 150 cm3 of water and dried over magnesium sulfate.



  The solvent is evaporated off in vacuo and the residue is chromatographed over aluminum oxide, the N- [2'-oxo-5'-methyl-oxazolidinyl- (3] -3-sulfamyl-4-chlorobenzoic acid amide) with a solvent mixture of ethyl acetate / methanol ( 9: 1) After recrystallization from chloroform / methanol (9: 1) the sulfonamide derivative melts at 215-216.



   PATENT CLAIM
Process for the preparation of the previously unknown N-12'-oxo-5'-methyl-oxazolidinyl- (3 ')] -3-sulfamyl-4-chlorobenzoic acid amide of the formula I.
EMI1.2
 characterized in that 3-sulfamyl-4-chlorobenzoyl chloride is reacted with 3-amino-5-methyl-oxazolidone- (2).

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines neuen Hydrazin-Derivates Es wurde gefunden, dass man zum bisher unbekannten N- [2'-Oxo-5'-methyloxazolidinyl- (3')]-3- sulfamyl-4-chlor-benzoesäureamid der Formel I EMI1.1 gelangt, indem man 3-Sulfamyl-4-chlor-benzoylchlorid mit 3-Amino-5-methyl-oxazolidon- (2) umsetzt. Process for the preparation of a new hydrazine derivative It has been found that the previously unknown N- [2'-oxo-5'-methyloxazolidinyl- (3 ')] -3-sulfamyl-4-chloro-benzoic acid amide of the formula I EMI1.1 obtained by reacting 3-sulfamyl-4-chlorobenzoyl chloride with 3-amino-5-methyl-oxazolidone- (2). Beispiel N- [2'-Oxo-5'-methyl-oxazolidinyl- (3')]- 3-sulfamyl-4-chlor-benzoesäureamid Eine Lösung von 3,5 g 3-Amino-5-methyl-oxa- zolidon- (2) und 3,0 g Triäthylarmin in 150 cm3 Chloroform wird unter Rühren bei 20-25 innert 30 Minuten mit 7,6 g 3-Sulfamyl-4-chlor-benzoyl- chlorid versetzt. Darauf wird die Reaktionslösung während 60 Stunden bei Zimmertemperatur weitergerührt, wobei sich eine schmierige Masse ausschei- det. Man dampft im Vakuum zur Trockne ein, versetzt den Eindampfrückstand mit 300 cm8 Essigsäureäthylester und 150 cm Wasser und schüttelt gut durch. example N- [2'-Oxo-5'-methyl-oxazolidinyl- (3 ')] - 3-sulfamyl-4-chloro-benzoic acid amide A solution of 3.5 g of 3-amino-5-methyl-oxazolidone- (2) and 3.0 g of triethyl amine in 150 cm3 of chloroform is mixed with 7.6 g of 3-sulfamyl within 30 minutes while stirring at 20-25 -4-chloro-benzoyl chloride added. The reaction solution is then stirred for a further 60 hours at room temperature, a greasy mass separating out. It is evaporated to dryness in vacuo, the residue from evaporation is mixed with 300 cm8 of ethyl acetate and 150 cm of water and shaken well. Nach Trennung der Schichten wird die Essigsäureäthylesterlösung mit total 150 cm3 Wasser gewaschen und über Magnesiumsulfat getrocknet. After separating the layers, the ethyl acetate solution is washed with a total of 150 cm3 of water and dried over magnesium sulfate. Das Lösungsmittel wird im Vakuum abgedampft und der Rückstand über Aluminiumoxyd chromatogra- phiert wobei das N- [2'-Oxo-5'-methyl-oxazolidinyl- (3]-3-sulfamyl-4-chlorbenzoesäureamid mit einem Lösungsmittelgemisch von Essigsaureäthylester/ Methanol (9 : 1) eluiert wird. Nach Umkristallisieren aus Chloroform/Methanol (9 : 1) schmilzt das Sulfon- amid-Derivat bei 215-216 . The solvent is evaporated off in vacuo and the residue is chromatographed over aluminum oxide, the N- [2'-oxo-5'-methyl-oxazolidinyl- (3] -3-sulfamyl-4-chlorobenzoic acid amide) with a solvent mixture of ethyl acetate / methanol ( 9: 1) After recrystallization from chloroform / methanol (9: 1) the sulfonamide derivative melts at 215-216. PATENTANSPRUCH Verfahren zur Herstellung des bisher unbekannten N-12'-Oxo-5'-methyl-oxazolidinyl-(3')]-3-sulfamyl- 4-chlor-benzoesäureamids der Formel I EMI1.2 dadurch gekennzeichnet, dass man 3-Sulfamyl-4-chlorbenzoylchlorid mit 3-Amino-5-methyl-oxazolidon- (2) umsetzt. PATENT CLAIM Process for the preparation of the previously unknown N-12'-oxo-5'-methyl-oxazolidinyl- (3 ')] -3-sulfamyl-4-chlorobenzoic acid amide of the formula I. EMI1.2 characterized in that 3-sulfamyl-4-chlorobenzoyl chloride is reacted with 3-amino-5-methyl-oxazolidone- (2).
CH1518664A 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative CH414641A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1518664A CH414641A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH1254760A CH396905A (en) 1960-11-09 1960-11-09 Process for the preparation of new hydrazine derivatives
CH1354460 1960-12-02
CH654761A CH418335A (en) 1960-11-09 1961-06-06 Process for the preparation of new hydrazine derivatives
CH1518664A CH414641A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative
CH1047461 1961-09-11
CH1518864A CH412892A (en) 1960-11-09 1961-09-11 Process for the preparation of new hydrazine derivatives

Publications (1)

Publication Number Publication Date
CH414641A true CH414641A (en) 1966-06-15

Family

ID=27561118

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1518664A CH414641A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative

Country Status (1)

Country Link
CH (1) CH414641A (en)

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