CH412895A - Process for the preparation of a new hydrazine derivative - Google Patents

Process for the preparation of a new hydrazine derivative

Info

Publication number
CH412895A
CH412895A CH1518764A CH1518764A CH412895A CH 412895 A CH412895 A CH 412895A CH 1518764 A CH1518764 A CH 1518764A CH 1518764 A CH1518764 A CH 1518764A CH 412895 A CH412895 A CH 412895A
Authority
CH
Switzerland
Prior art keywords
sulfamyl
chloro
acid amide
dimethyl
pyrrolyl
Prior art date
Application number
CH1518764A
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 CH1518764A priority Critical patent/CH412895A/en
Priority claimed from CH654761A external-priority patent/CH418335A/en
Publication of CH412895A publication Critical patent/CH412895A/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
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/50—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)

Description

       

  



  Verfahren zur Herstellung eines neuen Hydrazin-Derivates
Es wurde gefunden, dass man zum bisher   unbe-    kannten N-[2',5'-Dimethyl-pyrrolyl-1')]-3-sulfamyl4-chlor-benzoesÏureamid der Formel I
EMI1.1     
 gelangt, indem man 3-Sulfamyl-4-chlor-benzoylchlorid mit 1-Amino-2,5-dimethyl-pyrrol umsetzt.



   Beispiel
N-[2',5'-Dimethy-pyrrolyl-(1')]-3-sulfamyl   4-chlor-benzoesaureamid   
Eine Lösung von 2,   2g 1-Amino-2, 5-dimethyl-    pyrrol und 2, 1 g Triäthylamin in 100   ccm Chloro-    form wird unter Rühren bei   20-25     innert 15 Min. mit 5, 0 g 3-Sulfamyl-4-chlor-benzoylchlorid versetzt und das Reaktionsgemisch   anschliessend    72 Std. bei Zimmertemperatur   weitergerihrt.    Darauf wird das Reaktionsgemisch im Vakuum zur Trockne   abge-    dampft, der Rückstand mit 300 ccm Essigsäureäthylester und 100 ccm Wasser versetzt und   gut durch-    geschüttelt. Die organische Phase wird abgetrennt,  ber Magnesiumsulfat getrocknet und der   Essigsäurek    äthylester im Vakuum abdestilliert.

   Der Rückstand wird anschliessend  ber Aluminimumoxyd chromato  graphiert,    wobei das   N-[2', 5'-Dimethyl-pyrrolyll')]-    3-sulfamyl-4-chlor-benzoesÏureamid mit einem   Li    sungsmittelgemisch von Chloroform/Methanol (9 : 1) eluiert wird. Nach Umkristallisieren aus demselben Lösungsmittelgemisch schmilzt das Sulfonamid-Deri  vat bei 209-211 .     



   PATENTANSPRUCH
Verfahren zur Herstellung des bisher unbekannten N-   [2',    5'-Dimethyl-pyrrolyl-   (1')]-3-sulfamyl-4-      chlor-benzoesäureamids    der Formel I
EMI1.2     
 dadurch gekennzeichnet, dass man 3-Sulfamyl-4  chlor-benzoylchlorid    mit 1-Amino-2, 5-dimethyl-pyrrol 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 ', 5'-dimethyl-pyrrolyl-1')] -3-sulfamyl4-chloro-benzoic acid amide of the formula I
EMI1.1
 obtained by reacting 3-sulfamyl-4-chloro-benzoyl chloride with 1-amino-2,5-dimethyl-pyrrole.



   example
N- [2 ', 5'-Dimethy-pyrrolyl- (1')] - 3-sulfamyl 4-chloro-benzoic acid amide
A solution of 2.2 g of 1-amino-2,5-dimethylpyrrole and 2.1 g of triethylamine in 100 cc of chloroform is mixed with 5.0 g of 3-sulfamyl-4 within 15 minutes while stirring at 20-25 -chlorobenzoyl chloride is added and the reaction mixture is then stirred for a further 72 hours at room temperature. The reaction mixture is then evaporated to dryness in vacuo, 300 cc of ethyl acetate and 100 cc of water are added to the residue and the mixture is shaken well. The organic phase is separated off, dried over magnesium sulfate and the ethyl acetate is distilled off in vacuo.

   The residue is then chromatographed over aluminum oxide, the N- [2 ', 5'-dimethylpyrrolyll')] - 3-sulfamyl-4-chlorobenzoic acid amide eluting with a solvent mixture of chloroform / methanol (9: 1) becomes. After recrystallization from the same solvent mixture, the sulfonamide derivative melts at 209-211.



   PATENT CLAIM
Process for the preparation of the previously unknown N- [2 ', 5'-dimethyl-pyrrolyl- (1')] -3-sulfamyl-4-chloro-benzoic acid amide of the formula I.
EMI1.2
 characterized in that 3-sulfamyl-4 chlorobenzoyl chloride is reacted with 1-amino-2,5-dimethyl-pyrrole.

** 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 unbe- kannten N-[2',5'-Dimethyl-pyrrolyl-1')]-3-sulfamyl4-chlor-benzoesÏureamid der Formel I EMI1.1 gelangt, indem man 3-Sulfamyl-4-chlor-benzoylchlorid mit 1-Amino-2,5-dimethyl-pyrrol umsetzt. Process for the preparation of a new hydrazine derivative It has been found that the previously unknown N- [2 ', 5'-dimethyl-pyrrolyl-1')] -3-sulfamyl4-chloro-benzoic acid amide of the formula I EMI1.1 obtained by reacting 3-sulfamyl-4-chloro-benzoyl chloride with 1-amino-2,5-dimethyl-pyrrole. Beispiel N-[2',5'-Dimethy-pyrrolyl-(1')]-3-sulfamyl 4-chlor-benzoesaureamid Eine Lösung von 2, 2g 1-Amino-2, 5-dimethyl- pyrrol und 2, 1 g Triäthylamin in 100 ccm Chloro- form wird unter Rühren bei 20-25 innert 15 Min. mit 5, 0 g 3-Sulfamyl-4-chlor-benzoylchlorid versetzt und das Reaktionsgemisch anschliessend 72 Std. bei Zimmertemperatur weitergerihrt. Darauf wird das Reaktionsgemisch im Vakuum zur Trockne abge- dampft, der Rückstand mit 300 ccm Essigsäureäthylester und 100 ccm Wasser versetzt und gut durch- geschüttelt. Die organische Phase wird abgetrennt, ber Magnesiumsulfat getrocknet und der Essigsäurek äthylester im Vakuum abdestilliert. example N- [2 ', 5'-Dimethy-pyrrolyl- (1')] - 3-sulfamyl 4-chloro-benzoic acid amide A solution of 2.2 g of 1-amino-2,5-dimethylpyrrole and 2.1 g of triethylamine in 100 cc of chloroform is mixed with 5.0 g of 3-sulfamyl-4 within 15 minutes while stirring at 20-25 -chlorobenzoyl chloride is added and the reaction mixture is then stirred for a further 72 hours at room temperature. The reaction mixture is then evaporated to dryness in vacuo, 300 cc of ethyl acetate and 100 cc of water are added to the residue and the mixture is shaken well. The organic phase is separated off, dried over magnesium sulfate and the ethyl acetate is distilled off in vacuo. Der Rückstand wird anschliessend ber Aluminimumoxyd chromato graphiert, wobei das N-[2', 5'-Dimethyl-pyrrolyll')]- 3-sulfamyl-4-chlor-benzoesÏureamid mit einem Li sungsmittelgemisch von Chloroform/Methanol (9 : 1) eluiert wird. Nach Umkristallisieren aus demselben Lösungsmittelgemisch schmilzt das Sulfonamid-Deri vat bei 209-211 . The residue is then chromatographed over aluminum oxide, the N- [2 ', 5'-dimethylpyrrolyll')] - 3-sulfamyl-4-chlorobenzoic acid amide eluting with a solvent mixture of chloroform / methanol (9: 1) becomes. After recrystallization from the same solvent mixture, the sulfonamide derivative melts at 209-211. PATENTANSPRUCH Verfahren zur Herstellung des bisher unbekannten N- [2', 5'-Dimethyl-pyrrolyl- (1')]-3-sulfamyl-4- chlor-benzoesäureamids der Formel I EMI1.2 dadurch gekennzeichnet, dass man 3-Sulfamyl-4 chlor-benzoylchlorid mit 1-Amino-2, 5-dimethyl-pyrrol umsetzt. PATENT CLAIM Process for the preparation of the previously unknown N- [2 ', 5'-dimethyl-pyrrolyl- (1')] -3-sulfamyl-4-chloro-benzoic acid amide of the formula I. EMI1.2 characterized in that 3-sulfamyl-4 chlorobenzoyl chloride is reacted with 1-amino-2,5-dimethylpyrrole.
CH1518764A 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative CH412895A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1518764A CH412895A (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
CH1518764A CH412895A (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
CH412895A true CH412895A (en) 1966-05-15

Family

ID=27561119

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1518764A CH412895A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative

Country Status (1)

Country Link
CH (1) CH412895A (en)

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