DE1287589B - Process for the preparation of hydrazine compounds - Google Patents

Process for the preparation of hydrazine compounds

Info

Publication number
DE1287589B
DE1287589B DEV28134A DEV0028134A DE1287589B DE 1287589 B DE1287589 B DE 1287589B DE V28134 A DEV28134 A DE V28134A DE V0028134 A DEV0028134 A DE V0028134A DE 1287589 B DE1287589 B DE 1287589B
Authority
DE
Germany
Prior art keywords
hydrazine
preparation
hydrazine compounds
compounds
formula
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.)
Pending
Application number
DEV28134A
Other languages
German (de)
Inventor
Dipl-Chem Dr Hubertus
Pietzrzok
Schindler
Dipl-Chem Dr Wolfgang
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.)
Filmfabrik Wolfen VEB
Original Assignee
Filmfabrik Wolfen VEB
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 Filmfabrik Wolfen VEB filed Critical Filmfabrik Wolfen VEB
Priority to DEV28134A priority Critical patent/DE1287589B/en
Publication of DE1287589B publication Critical patent/DE1287589B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5

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

Description

Die Erfindung betrifft ein Verfahren zur Herstellung von Hydrazinverbindungen der allgemeinen FormelThe invention relates to a process for the preparation of hydrazine compounds of the general formula

HO3S — (CH2)J1 — NH — NH — R
in der R Wasserstoff, -CONH2, -CSNH2 oder NH2-C = NHHO 3 S - (CH 2 ) J 1 - NH - NH - R
in which R is hydrogen, -CONH 2 , -CSNH 2 or NH 2 -C = NH

und κ 2 bis 4 bedeutet. Das Verfahren ist dadurch gekennzeichnet, daß man Sultone der Formeland κ is 2-4. The procedure is through characterized in that one sultones of the formula

(CHa)n-SO2 (CHa) n -SO 2

1010

1515th

mit Hydrazinhydrat (N2H4 · H2O) oder Hydrazinverbindungen der Formel NH2 — NH — R umsetzt, wobei R und η die oben angegebene Bedeutung besitzen.with hydrazine hydrate (N 2 H 4 · H 2 O) or hydrazine compounds of the formula NH 2 - NH - R, where R and η have the meanings given above.

Es ist bereits bekannt, Hydrazino-alkylsulfonsäuren ao durch Anlagerung von Hydrazinhydrat an Alkenylsulfonsäuren herzustellen. Die dabei entstandenen Hydrazinverbindungen sind nur in Form ihrer Benzalverbindung isolierbar, deren Spaltung mit konzentrierter Salzsäure dann erst die freie Hydrazin- as verbindung liefert. Das bekannte Verfahren ist also umständlich und zeitraubend.It is already known to hydrazino-alkylsulfonic acids ao by adding hydrazine hydrate to alkenyl sulfonic acids. The resulting Hydrazine compounds can only be isolated in the form of their benzal compound, their cleavage with concentrated hydrochloric acid then the free hydrazine as connection supplies. The known method is therefore cumbersome and time-consuming.

Der Erfindung liegt die Aufgabe zugrunde, diese wasserlöslichen Hydrazinverbindungen in einfacher Weise herzustellen.The invention is based on the object of providing these water-soluble hydrazine compounds in a simple manner Way to manufacture.

Es war durchaus nicht zu erwarten, daß die Umsetzung gemäß der Erfindung in derartig eindeutiger Weise vonstatten geht und die Hydrazinverbindungen in guter Ausbeute und großer Reinheit erhalten werden. Vielmehr ist es bekannt, daß bei ähnlichen Reaktionen zumindest zwei verschiedene Verbindungen nebeneinander entstehen, z. B. eine Mono- und eine Bis-Verbindung, deren Reinigung und Abtrennung sehr schwierig sind.It was by no means to be expected that the implementation according to the invention would be as unambiguous as this Manner and the hydrazine compounds are obtained in good yield and high purity. Rather, it is known that in similar reactions at least two different compounds arise side by side, z. B. a mono- and a bis-compound, their purification and separation are very difficult.

In der pharmazeutischen und fotografischen Industrie besteht großes Interesse an diesen Hydrazinverbindungen, die z. B. als Zwischenprodukte für die Herstellung von Pyrazolonen-(5), Pyrazolidin-dionen-(3,5) oder davon abgeleiteten Verbindungen verwendet werden.In the pharmaceutical and photographic industries there is great interest in these hydrazine compounds, e.g. B. as intermediates for the Preparation of pyrazolones- (5), pyrazolidine-dione- (3,5) or compounds derived therefrom will.

Beispiel 1example 1

HO3S — (CHg)4 — NH — NH2 HO 3 S - (CHg) 4 - NH - NH 2

Zu 100 g 60%iger wäßriger Lösung von Hydrazinhydrat werden unter Umschütteln 28 g Butansulton in mehreren kleinen Portionen zugegeben. Die dabei entstehende heftige exotherme Reaktion wird durch Kühlung des Reaktionsgefäßes mit Wasser verlangsamt. Nach Beendigung der Reaktion läßt man das Gemisch 2 Stunden stehen und destilliert das überschüssige Hydrazinhydrat im Vakuum ab. Den sirupösen Rückstand nimmt man mit 300 ml Methanol auf, kühlt die Lösung auf O0C ab und fällt anschließend die Hydrazinverbindung durch Zugabe von Tetrachlorkohlenstoff aus. Man erhält 33,5 g (theoretische Ausbeute). Die farblosen Kristalle besitzen nach Reinigung mit Methanol einen Schmelzpunkt von 163 bis 1650C.To 100 g of 60% strength aqueous solution of hydrazine hydrate, 28 g of butane sultone are added in several small portions with shaking. The resulting violent exothermic reaction is slowed down by cooling the reaction vessel with water. After the reaction has ended, the mixture is left to stand for 2 hours and the excess hydrazine hydrate is distilled off in vacuo. The syrupy residue is taken up in 300 ml of methanol, the solution is cooled to 0 ° C. and the hydrazine compound is then precipitated by adding carbon tetrachloride. 33.5 g are obtained (theoretical yield). After purification with methanol, the colorless crystals have a melting point of 163 to 165 ° C.

Beispiel 2Example 2

HO3S — (CH2)3 — NH — NH2 HO 3 S - (CH 2 ) 3 - NH - NH 2

Zu 50 g wäßrigem 50%igem Hydrazinhydrat werden unter Umschütteln 12,2 g Propansulton zugesetzt. Nach Beendigung der stark exothermen Reaktion, die wie im Beispiel 1 durch äußere Kühlung gemäßigt wird, behandelt man das Gemisch weiter, wie im Beispiel 1 angegeben. Man erhält 12 g (78 % der Theorie) farblose Kristalle. Sie werden aus einer Lösung von Methanol und Propanol (1:1) umkristallisiert und schmelzen bei 195 bis 197° C.To 50 g of aqueous 50% hydrazine hydrate, 12.2 g of propane sultone are added with shaking. After the strongly exothermic reaction has ended, which, as in Example 1, is moderated by external cooling the mixture is treated further as indicated in Example 1. 12 g (78% of Theory) colorless crystals. They are recrystallized from a solution of methanol and propanol (1: 1) and melt at 195 to 197 ° C.

Beispiel 3Example 3

HO3S — (CHa)4 — NH — NH — CS — NH2 HO 3 S - (CHa) 4 - NH - NH - CS - NH 2

9,1 g Thiosemicarbazid werden in 100 ml wäßrigem 50%igem Methanol gelöst. Der Lösung werden bei Zimmertemperatur unter Umschütteln 14 g Butansulton zugesetzt. Man läßt das Gemisch mindestens 20 Stunden stehen und destilliert dann das Lösungsmittel im Vakuum ab. Dem so erhaltenen klaren viskosen Rückstand werden nach mehrtägigem Stehen nochmals 100 ml Methanol zugegeben. Das Gemisch wird kurz aufgekocht. Man erhält nach Abkühlung 12 g (53% der Theorie) farblose Kristalle, die aus Äthylalkohol umkristallisiert werden und dann bei 195 bis 196 0C schmelzen.9.1 g of thiosemicarbazide are dissolved in 100 ml of aqueous 50% strength methanol. 14 g of butane sultone are added to the solution at room temperature with shaking. The mixture is left to stand for at least 20 hours and the solvent is then distilled off in vacuo. A further 100 ml of methanol are added to the clear, viscous residue obtained in this way after standing for several days. The mixture is briefly boiled. After cooling to obtain 12 g (53% of theory) of colorless crystals, which are recrystallized from ethyl alcohol and then melting at 195-196 0 C.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von Hydrazinverbindungen der allgemeinen FormelProcess for the preparation of hydrazine compounds of the general formula HO3S — (CH2V — NH — NH — RHO 3 S - (CH 2 V - NH - NH - R in der R Wasserstoff, — CONH2, — CSNH2 oderin which R is hydrogen, - CONH 2 , - CSNH 2 or NH2 — C = NHNH 2 - C = NH und η 2 bis 4 bedeutet, dadurch gekennzeichnet, daß Sultone der Formeland η is 2 to 4, characterized in that sultones of the formula (CHj)n — SO2 (CHj) n - SO 2 O-O- mit Hydrazinhydrat oder Hydrazinverbindungen der Formel NH2 — NH — R umgesetzt werden, wobei R und η die oben angegebene Bedeutung besitzen.with hydrazine hydrate or hydrazine compounds of the formula NH 2 - NH - R, where R and η have the meanings given above.
DEV28134A 1965-03-25 1965-03-25 Process for the preparation of hydrazine compounds Pending DE1287589B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEV28134A DE1287589B (en) 1965-03-25 1965-03-25 Process for the preparation of hydrazine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEV28134A DE1287589B (en) 1965-03-25 1965-03-25 Process for the preparation of hydrazine compounds

Publications (1)

Publication Number Publication Date
DE1287589B true DE1287589B (en) 1969-01-23

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEV28134A Pending DE1287589B (en) 1965-03-25 1965-03-25 Process for the preparation of hydrazine compounds

Country Status (1)

Country Link
DE (1) DE1287589B (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE696776C (en) * 1938-08-16 1940-09-28 I G Farbenindustrie Akt Ges Process for the preparation of hydrazinoalkylsulfonic acids
DE1095841B (en) * 1959-02-18 1960-12-29 Bayer Ag Process for the preparation of alkyl-substituted hydrazines
DE1108233B (en) * 1959-10-09 1961-06-08 Bayer Ag Process for the preparation of hydrazine derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE696776C (en) * 1938-08-16 1940-09-28 I G Farbenindustrie Akt Ges Process for the preparation of hydrazinoalkylsulfonic acids
DE1095841B (en) * 1959-02-18 1960-12-29 Bayer Ag Process for the preparation of alkyl-substituted hydrazines
DE1108233B (en) * 1959-10-09 1961-06-08 Bayer Ag Process for the preparation of hydrazine derivatives

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