CH340828A - Process for the preparation of new 3,5-dioxo-pyrazolidines - Google Patents

Process for the preparation of new 3,5-dioxo-pyrazolidines

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Publication number
CH340828A
CH340828A CH340828DA CH340828A CH 340828 A CH340828 A CH 340828A CH 340828D A CH340828D A CH 340828DA CH 340828 A CH340828 A CH 340828A
Authority
CH
Switzerland
Prior art keywords
dioxo
new
pyrazolidines
preparation
diphenyl
Prior art date
Application number
Other languages
German (de)
Inventor
Josef Dr Ctvrtnik
Oldrich Dr Nemecek
Mayer Jiri
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH340828A publication Critical patent/CH340828A/en

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Description

  

  Verfahren zur     Herstellung    von neuen     3,5-Dioxo-pyrazolidinen       Gegenstand des vorliegenden Patentes ist ein       Verfahren    zur Herstellung von neuen     1,2-Diphenyl-          3,5-dioxo-4-halogenalkenyl-pyrazolidinen.    Das Ver  fahren ist dadurch gekennzeichnet, dass man     1,2-          Diphenyl-3,5-dioxo-pyrazolidin    mit     Halogenalkenen,     die mindestens 1 Halogenatom an einem einfach  gebundenen     Kohlenstoffatom    und mindestens ein  Halogenatom an einem doppelt gebundenen Kohlen  stoffatom besitzen, umsetzt.  



  Als     Halogenalkene    kommen z. B.     1,3-Dichlor-          hexadien-3,5,        Trichlorhexene    und insbesondere     1,3-          Dichlor-buten-2    in Frage. Diese Stoffe können leicht  aus Abfällen der     Chloroprenfabrikation    gewonnen  werden.  



  Die erhaltenen neuen     1,2-Diphenyl-3,5-dioxo-4-          halogenalkenyl-pyrazolidine    sind kristalline, farblose  Verbindungen. Sie sollen als Zwischenprodukte für  die Herstellung von antirheumatischen Wirkstoffen  Verwendung finden.  



  <I>Beispiel</I>  24,8 Gewichtsteile     1,2-Diphenyl-3,5-dioxo-          pyrazolidin    werden in 1     Mol    verdünnter Natronlauge  aufgelöst und dann werden 12,5 Gewichtsteile     1,3-          Dichlor-buten-2    langsam unter Rühren     zutropfen    ge  lassen. Nachher wird das Gemisch noch 15 Minuten    bei 20-50  C gerührt. Dann wird abgekühlt und  die Lösung mit Benzol oder mit einem andern,     mit     Wasser nicht mischbaren Lösungsmittel ausgeschüt  telt.

   Der     wässrige,    das     Natriumsalz    des Reaktions  produktes enthaltende     Anteil    wird mit     Hilfe    von  Aktivkohle entfärbt und mit einer anorganischen  oder organischen Säure kongosauer gestellt. Der  Niederschlag, das     1,2-Diphenyl-3,5-dioxo-4-y-chlor-          crotyl-pyrazolidin,    bildet nach dem     Umkristallisieren     aus     wässrigem    Äthanol oder Aceton farblose Nadeln  und schmilzt bei 167-168  C     (korr.)  



  Process for the preparation of new 3,5-dioxo-pyrazolidines The present patent relates to a process for the preparation of new 1,2-diphenyl-3,5-dioxo-4-haloalkenyl-pyrazolidines. The process is characterized in that 1,2-diphenyl-3,5-dioxo-pyrazolidine is reacted with haloalkenes which have at least 1 halogen atom on a single bonded carbon atom and at least one halogen atom on a double bonded carbon atom.



  As halogen alkenes such. B. 1,3-dichloro-hexadiene-3,5, trichlorohexene and especially 1,3-dichloro-2-butene are possible. These substances can easily be obtained from waste from chloroprene production.



  The new 1,2-diphenyl-3,5-dioxo-4-haloalkenylpyrazolidines obtained are crystalline, colorless compounds. They should be used as intermediate products for the production of anti-rheumatic agents.



  <I> Example </I> 24.8 parts by weight of 1,2-diphenyl-3,5-dioxopyrazolidine are dissolved in 1 mol of dilute sodium hydroxide solution and then 12.5 parts by weight of 1,3-dichloro-2-butene are slowly added Add dropwise stirring. The mixture is then stirred at 20-50 ° C. for a further 15 minutes. It is then cooled and the solution extracted with benzene or with another water-immiscible solvent.

   The aqueous portion containing the sodium salt of the reaction product is decolorized with the aid of activated charcoal and acidified to Congo with an inorganic or organic acid. The precipitate, the 1,2-diphenyl-3,5-dioxo-4-y-chlorocrotyl-pyrazolidine, forms colorless needles after recrystallization from aqueous ethanol or acetone and melts at 167-168 C (corr.)

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von neuen 1,2-Di- phenyl-3,5-Dioxo-4-halogenalkenyl-pyrazolidinen, da durch gekennzeichnet, dass man 1,2-Diphenyl-3,5- dioxo-pyrazolidin mit Halogenalkenen, die minde stens 1 Halogenatom an einem einfach. gebundenen Kohlenstoffatom und mindestens ein Halogenatom an einem doppelt gebundenen Kohlenstoffatom be sitzen, umsetzt. PATENT CLAIM Process for the production of new 1,2-diphenyl-3,5-dioxo-4-haloalkenyl-pyrazolidines, characterized in that 1,2-diphenyl-3,5-dioxo-pyrazolidine with haloalkenes, the min at least 1 halogen atom on a single. Bonded carbon atom and at least one halogen atom on a doubly bonded carbon atom be, reacted. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekenn zeichnet, dass man als Halogenalken 1,3-Dichlor- buten-2 verwendet. SUBCLAIM Process according to claim, characterized in that the halogen alkene used is 1,3-dichloro-2-butene.
CH340828D 1954-09-24 1955-04-06 Process for the preparation of new 3,5-dioxo-pyrazolidines CH340828A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CS340828X 1954-09-24
CS291054X 1954-10-29

Publications (1)

Publication Number Publication Date
CH340828A true CH340828A (en) 1959-09-15

Family

ID=25746750

Family Applications (1)

Application Number Title Priority Date Filing Date
CH340828D CH340828A (en) 1954-09-24 1955-04-06 Process for the preparation of new 3,5-dioxo-pyrazolidines

Country Status (1)

Country Link
CH (1) CH340828A (en)

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