DE1155773B - Process for the preparation of acylhydrazones - Google Patents

Process for the preparation of acylhydrazones

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Publication number
DE1155773B
DE1155773B DEF35469A DEF0035469A DE1155773B DE 1155773 B DE1155773 B DE 1155773B DE F35469 A DEF35469 A DE F35469A DE F0035469 A DEF0035469 A DE F0035469A DE 1155773 B DE1155773 B DE 1155773B
Authority
DE
Germany
Prior art keywords
chloride
bromo
acetylhydrazide
pyridinium
acylhydrazones
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
DEF35469A
Other languages
German (de)
Inventor
Dr Hans Wissmann
Dr Walter Siedel
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
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 Hoechst AG filed Critical Hoechst AG
Priority to DEF35469A priority Critical patent/DE1155773B/en
Priority to GB4597962A priority patent/GB1016654A/en
Publication of DE1155773B publication Critical patent/DE1155773B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Description

DEUTSCHESGERMAN

PATENTARiTPATENTARY

kl. 12 ο 22 kl. 12 ο 22

INTERNATIONALE KL.INTERNATIONAL KL.

C07c;dC07c; d

F35469IVb/12oF35469IVb / 12o

ANMELDETAG: 5. DEZEMBER 1961REGISTRATION DATE: DECEMBER 5, 1961

BEKANNTMACHUNG
DER ANMELDUNG
UNDAUSGABEDER
AUSLEGESCHRIFT: 17. OKTOBER 1963 NOTICE
THE REGISTRATION
ANDOUTPUTE
EDITORIAL: OCTOBER 17, 1963

Es ist bereits bekannt, daß in bestimmter Weise kernsubstituierte x-Halogen-zimtaldehyde bakteriostatische und fungistatische Eigenschaften besitzen (vgl. The Indian Journal of Pharmacy, 14 [1952], S. 3 bis 5, und 18 [1956], S. 396 bis 401, sowie deutsche Auslegeschrift 1 103 318). Die geringe Wasserlöslichkeit dieser bekannten Verbindungen bedingt jedoch die Verwendung von Lösungsvermittlern.It is already known that in a certain way nucleus-substituted x-halo-cinnamaldehydes are bacteriostatic and have fungistatic properties (cf. The Indian Journal of Pharmacy, 14 [1952], Pp. 3 to 5, and 18 [1956], pp. 396 to 401, as well as German Auslegeschrift 1 103 318). The low water solubility However, these known compounds require the use of solubilizers.

Es wurde gefunden, daß man Acylhydrazone mit guten Ausbeuten erhält, wenn man x-Brom-zimtaldehyde der allgemeinen FormelIt has been found that acylhydrazones are obtained in good yields if x-bromo-cinnamaldehydes are used the general formula

Verfahren zur Herstellung
von AcylhydrazonenMethod of manufacture
of acylhydrazones

-CH = C-CHO-CH = C-CHO

BrBr

worin R für Chlor, Brom, die Nitrogruppe oder die Cyangruppe steht, in alkoholischen Lösungsmitteln und in Gegenwart von Säuren mit Trimethylammonium-acetylhydrazidchlorid oder Pyridinium-acetylhydrazidchlorid zur Umsetzung bringt, und daß die so erhaltenen Verfahrenserzeugnisse eine wesentlich bessere biologische Wirkung entfalten und eine 100-bis 200mal größere Wasserlöslichkeit besitzen als die vorerwähnten bekannten entsprechenden Aldehyde. Das Verfahren gemäß der Erfindung wird in alkoholischen Lösungsmitteln durchgeführt, wobei als solche vorteilhaft aliphatische Alkohole mit 1 bis 4 Kohlenstoffatomen verwendet werden. Man arbeitet ferner in Gegenwart von Säuren, von denen beispielsweise Halogenwasserstoffsäuren wie Salzsäure oder Schwefelsäure bzw. organische Säuren wie Essigsäure oder Ameisensäure verwendet werden. Die Umsetzung wird zweckmäßig in der Weise durchgeführt, daß die als Ausgangsstoffe verwendeten Λ-Brom-zimtaldehyde Anmelder:where R stands for chlorine, bromine, the nitro group or the cyano group, in alcoholic solvents and in the presence of acids with trimethylammonium acetylhydrazide chloride or pyridinium acetylhydrazide chloride to the reaction, and that the process products thus obtained are an essential develop better biological effects and have 100 to 200 times greater water solubility than the aforementioned known corresponding aldehydes. The method according to the invention is carried out in alcoholic Solvents carried out, as such advantageously aliphatic alcohols with 1 to 4 carbon atoms are used. You also work in the presence of acids, of which, for example Hydrogen halide acids such as hydrochloric acid or sulfuric acid or organic acids such as acetic acid or formic acid can be used. The reaction is expediently carried out in such a way that the Λ-bromocinnamaldehyde used as starting materials Applicant:

Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft

vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,

Frankfurt/M.Frankfurt / M.

Dr. Hans Wissmann, Frankfurt/M.-Unterliederbach, und Dr. Walter Siedel, Bad Soden (Taunus),Dr. Hans Wissmann, Frankfurt / M.-Unterliederbach, and Dr. Walter Siedel, Bad Soden (Taunus),

sind als Erfinder genannt wordenhave been named as inventors

in alkoholischer Lösung vorgelegt und nach Zusatz der Säuren ebenfalls in alkoholischer Lösung mit einer Suspension von Trimethylammoniurn-acetylhydrazidchlorid bzw. Pyridinium-acetylhydrazidchlorid versetzt werden. Die Reaktion selbst wird vorteilhaft bei mäßig erhöhter Temperatur, insbesondere bei der Siedetemperatur des verwendeten Lösungsmittels, vorgenommen. Im allgemeinen fallen die gewünschten Verfahrenserzeugnisse aus der alkoholischen Reaktionslösung in kristallisierter Form aus. Sollte infolge zu hoher Löslichkeit der Verfahrensprodukte eine derartige Kristallisierung nicht sofort erfolgen, so kann auch eine Ausfällung mit beispielsweise Diäthyläther vorgenommen werden.presented in alcoholic solution and after adding the acids also in alcoholic solution with a Suspension of trimethylammonium acetylhydrazide chloride or pyridinium acetylhydrazide chloride are added will. The reaction itself becomes advantageous at a moderately elevated temperature, especially at the boiling point of the solvent used. In general, those that are desired fall Process products from the alcoholic reaction solution in crystallized form. Should as a result too high solubility of the process products such crystallization cannot take place immediately precipitation can also be carried out with, for example, diethyl ether.

Die Verfahrenserzeugnisse der Formel
RThe process products of the formula
R.

• — CH = C — CH = N — NH — CO — CH2- N(CH3)3 Br• - CH = C - CH = N - NH - CO - CH 2 - N (CH 3 ) 3 Br

' — CH = C — CH = N — NH — CO — CH2 — N'- CH = C - CH = N - NH - CO - CH 2 - N

BrBr

ClCl

+
Cl+
Cl

309 728/281309 728/281

worin R die angegebene Bedeutung besitzt, stellen hochwirksame Fungistatika dar, die sich gegenüber bekannten Verbindungen vergleichbarer chemischer Struktur durch erheblich bessere Wirksamkeit auszeichnen. In der Tabelle I werden einige der neuen Verfahrenserzeugnisse hinsichtlich ihrer Wirksamkeit gegen Hautpilze, Soor und Verrottungspilze mit einschlägigen bekannten Verbindungen verglichen, wobeiin which R has the meaning given, represent highly effective fungistats, which oppose each other known compounds of comparable chemical structure are characterized by significantly better effectiveness. Table I lists some of the new process products in terms of their effectiveness against skin fungi, thrush and rotting fungi compared with relevant known compounds, whereby

die angegebenen Zahlen Konzentrationen der verschiedenen geprüften Verbindungen in v/ml darstellen, die ausreichend waren, um bei einer Versuchsdauer von etwa 18 Tagen das Wachstum der im einzelnen aufgeführten Pilze auf festen Nährböden völlig zu verhindern. Aus diesen Angaben ist die überlegene Wirksamkeit der Verfahrenserzeugnisse klar ersichtlich. the figures given represent concentrations of the various compounds tested in v / ml, which were sufficient for the growth of the individual with a test duration of about 18 days to prevent the listed fungi on solid culture media completely. From this information is the superior one Effectiveness of the process products clearly evident.

Tabelle ITable I.

Mifcro-
sporon
gypseumMifcro
sporon
gypseum Hau
Tricho-
phyton
rubrumHuh
Tricho-
phyton
rubrum ;pilze
Tricho-
phyton
tonsurans;mushrooms
Tricho-
phyton
tonsurans Tricho-
phyton
epilansTricho-
phyton
epilans S(
Candida
albicans
504S (
Candida
albicans
504 3or
Candida
albicans
Y 12003or
Candida
albicans
Y 1200 Verrott
Asper-
gillus
nigerRot
Asper
gillus
Niger ungspilze
Tricho-
■ derma
viridefungi
Tricho-
■ derma
viride 5-Chlorsalizyliden-trimethylammo-
nium-acetylhydrazidchlorid (vgl.
USA.-Patentschrift 2 670 348) ...5-chlorosalicylidene trimethylammo-
nium acetylhydrazide chloride (cf.
U.S. Patent 2,670,348) ... 6262 6262 6262 3131 500500 500500 500500 500500 5-ChlorsalizyIiden-pyridinium-ace-
tylhydrazidchlorid (vgl. USA.-
Patentschrift 2 670 348) 5-chlorosalizyliden-pyridinium-ace-
tylhydrazide chloride (see USA.-
Patent specification 2,670,348) 3131 3131 3131 3131 500500 500500 500500 500500 a-Brom-p-cyan-zimtaldehyd (vgl.
deutsche Auslegeschrift 1 103 318)a-bromo-p-cyano-cinnamaldehyde (cf.
German interpretation document 1 103 318) 6262 3131 3131 3131 500500 250250 > 1000> 1000 250250 «-Brom-p-nitro-zimtaldehyd (vgl.
Indian Journal of Pharmacy, 18
[1956], S. 396 «-Bromo-p-nitro-cinnamaldehyde (cf.
Indian Journal of Pharmacy, Jan.
[1956], p. 396 1616 1616 1616 1616 500500 250250 > 1000> 1000 10001000 «-Brom-p-chlorcinnamyliden-tri-
methylammonium-acetylhydrazid-
chlorid «-Bromo-p-chlorocinnamylidene-tri-
methylammonium acetylhydrazide
chloride 11 22 22 11 1616 1616 250250 6262 a-Brom-p-chlorcinnamyliden-pyr-
idinium-acetylhydrazidchlorid ...a-bromo-p-chlorocinnamylidene-pyr-
idinium acetylhydrazide chloride ... 44th 44th 44th 11 125125 125125 250250 125125 a-Brom-p-cyancinnamyliden-pyr-
idinium-acetylhydrazidchlorid ...a-bromo-p-cyancinnamylidene-pyr-
idinium acetylhydrazide chloride ... 88th 44th 44th 44th > 1000> 1000 125125 > 1000> 1000 500500

Von besonderer Bedeutung ist auch die erheblich bessere Wasserlöslichkeit der neuen Verfahrenserzeugnisse gegenüber vergleichbaren bekannten Verbindungen, die deren Eignung als Zusätze zu Desinfektionsmitteln, Seifen, Spülmitteln usw. begründet. In der nachstehenden Tabelle II sind die Löslichkeiten einiger der neuen Verfahrenserzeugnisse in Wasser bei 200C den entsprechenden Löslichkeiten von vergleichbaren bekannten Verbindungen gegenübergestellt, soOf particular importance is the significantly better water solubility of the new process products compared to comparable known compounds, which explains their suitability as additives to disinfectants, soaps, detergents, etc. In Table II below, the solubilities of some of the new process products in water at 20 ° C. are compared with the corresponding solubilities of comparable known compounds, see above

Tabelle IITable II

Tabelle II (Fortsetzung)Table II (continued)

Nr.No. Verbindunglink Löslichkeit
in Wasser
bei 20°Csolubility
in water
at 20 ° C 11 Λ-Brom-p-mtro-zimtaldehyd ...Λ-bromine-p-mtro-cinnamaldehyde ... < 0,0007%<0.0007% 22 «-Brom-p-cyan-zimtaldehyd ...«-Bromo-p-cyano-cinnamaldehyde ... < 0,000870 <0.00087 0 33 a-Brom-p-chlorzimtaldehyd a-bromo-p-chlorocinnamaldehyde 0,0008 ° Ό0.0008 ° Ό 44th «-Brom-p-chlorcinnamyliden-
trimethylammonium-acetyl-
hydrazidchlorid «-Bromo-p-chlorocinnamylidene-
trimethylammonium acetyl
hydrazide chloride 0,169%0.169% 55 a-Brom-p-chlorcinnamyliden-
pyridinium-acetylhydrazid-
chlorid a-bromo-p-chlorocinnamylidene-
pyridinium acetylhydrazide
chloride 0,09%0.09%

Nr.No. Verbindunglink Löslichkeit
in Wasser
bei 20° Csolubility
in water
at 20 ° C 6
7
86th
7th
8th Λ-Brom-p-nitrocinnamyliden-
trimethylammonium-acetyl-
hydrazidchlorid
a-Brom-p-nitrocinnamyliden-
pyridinium-acetylhydrazid-
chlorid
«-Brom-p-cyancinnamyliden-
pyridinium-acetylhydrazid-
chlorid Λ-bromo-p-nitrocinnamylidene-
trimethylammonium acetyl
hydrazide chloride
a-bromo-p-nitrocinnamylidene-
pyridinium acetylhydrazide
chloride
«-Brom-p-cyancinnamyliden-
pyridinium acetylhydrazide
chloride 0,22%
0,177%
0,119%0.22%
0.177%
0.119%

Beispiel 1example 1

ac - Brom -A- nitrocinnamyliden - trimethylammoniumacetylhydrazidchlorid 6 g a-Brom-4-nitro-zimtaldehyd werden in 90 ml absolutem Methanol heiß gelöst. Der Lösung wird nach Zusatz von 0,3 ml lOnormaler methanolischer Salzsäure und unter Umschütteln eine Suspension von 4,5 g Trimethylammonium-acetylhydrazidchlorid (Girard-Reagenz T) in 10 ml Methanol zugesetzt. Nach 15minutigem Kochen unter Rückfluß wird das Reaktionsgemisch gekühlt, das ausgefallene a. - Brom - 4 - nitrocinnamyliden - trimethylammonium- ac - bromo -A- nitrocinnamylidene - trimethylammoniumacetylhydrazide chloride 6 g of a-bromo-4-nitro-cinnamaldehyde are dissolved in 90 ml of absolute methanol while hot. After adding 0.3 ml of 10 normal methanolic hydrochloric acid and shaking, a suspension of 4.5 g of trimethylammonium acetylhydrazide chloride (Girard reagent T) in 10 ml of methanol is added to the solution. After refluxing for 15 minutes, the reaction mixture is cooled and the precipitated a. - bromine - 4 - nitrocinnamylidene - trimethylammonium-

acetylhydrazidchlorid abfiltriert, mit absolutem Äther gewaschen und getrocknet. Die Ausbeute beträgt 6,35 g (63% der Theorie); Schmelzpunkt: 194 bis 195°C.Acetylhydrazide chloride was filtered off, washed with absolute ether and dried. The yield is 6.35 g (63% of theory); Melting point: 194 to 195 ° C.

In analoger Weise werden, ausgehend von Trimethylammonium-acetylhydrazid, erhalten:In an analogous manner, starting from trimethylammonium acetylhydrazide, the following are obtained:

VerfahrensproduktProcess product UmsetzungskomponenteImplementation component SchmelzpunktMelting point Ausbeuteyield ^-Brom-4-chlorcinnamyliden-trimethylammo-
nium-acetylhydrazidchlorid
«-Brom^-chlorcinnamyliden-trimethylammo-
nium-acetylhydrazidchlorid^ -Bromo-4-chlorocinnamylidene-trimethylammo-
nium acetyl hydrazide chloride
«-Bromo ^ -chlorcinnamylidene-trimethylammo-
nium acetyl hydrazide chloride «-Brom-4-chlor-zimt-
aldehyd
ac-Brom-2-chlor-zimt-
aldehyd«-Bromo-4-chloro-cinnamon-
aldehyde
ac-bromo-2-chloro-cinnamon
aldehyde 210°C
191 bis 192° C210 ° C
191 to 192 ° C 80% der Theorie
63 % der Theorie80% of theory
63% of theory

Beispiel 2 aldehyd und Pyridinium - acetylhydrazidchlorid, χ - Brom - 4 - nitrocinnamyliden - pyridinium - acetyl- κ . Brom - 4 - nitrocinnamyliden - pyridinium - acetylhydrazidchlorid hydrazidchlorid vom Schmelzpunkt 2530C (unter Entsprechend der im Beispiel 1 angegebenen Vor- 20 Zersetzung) erhalten. Die Ausbeute beträgt 50% schrift wird, ausgehend von «-Brom-4-nitro-zimt- der Theorie.Example 2 aldehyde and pyridinium - acetylhydrazide chloride, χ - bromine - 4 - nitrocinnamylidene - pyridinium - acetyl- κ . Bromo - 4 - nitrocinnamyliden - pyridinium - acetylhydrazidchlorid hydrazidchlorid (20 decomposition According to the advantages indicated in Example 1) of melting point 253 0 C. The yield is 50%, based on “-Bromo-4-nitro-cinnamon” theory.

In analoger Weise werden, ausgehend vonIn an analogous way, starting from Pyridinium-acetylhydrazidchlorid, erhalten:Pyridinium acetylhydrazide chloride, obtained: SchmelzpunktMelting point Ausbeuteyield VerfahrensproduktProcess product UmsetzungskomponenteImplementation component 2660C (unter
Zersetzung)266 0 C (under
Decomposition) 60% der Theorie60% of theory «-Brom^-chlorcinnamyliden-pyridinium-
acetylhydrazidchlorid«-Bromo ^ -chlorcinnamylidene-pyridinium-
acetyl hydrazide chloride -Brom-4-chlor-zimt-
aldehyd-Bromo-4-chloro-cinnamon-
aldehyde 186bisl88°C186 to 188 ° C 86% der Theorie86% of theory *-Brom-2-chlorcinnamyliden-pyridinium-
acetylhydrazidchlorid* -Bromo-2-chlorocinnamylidene-pyridinium-
acetyl hydrazide chloride «-Brom-2-chlor-zimt-
aldehyd«-Bromo-2-chloro-cinnamon-
aldehyde 236° C236 ° C 30% der Theorie30% of theory S^-Dibrom-cinnamyliden-pyridinium-acetyl-
hydrazidchloridS ^ -dibromo-cinnamylidene-pyridinium-acetyl-
hydrazide chloride 3,«-Dibrom-zimtaldehyd3, «- Dibromocinnamaldehyde 266° C266 ° C 66% der Theorie66% of theory «-Brom-p-cyancinnamyliden-pyridinium-acetyl-
hydrazidchlorid«-Bromo-p-cyancinnamyliden-pyridinium-acetyl-
hydrazide chloride «-Brom-p-cyan-zimt-
aldehyd«-Brom-p-cyan-cinnamon-
aldehyde

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Herstellung von Acylhydrazonen, dadurch gekennzeichnet, daß man a-Brom-zimtaldehyde der allgemeinen FormelProcess for the preparation of acylhydrazones, characterized in that one uses α-bromo-cinnamaldehydes of the general formula \—CH = C-CHO\ -CH = C-CHO BrBr worin R für Chlor, Brom, die Nitrogruppe oder methylammonium-acetylhydrazidchlorid oder Pyr-where R is chlorine, bromine, the nitro group or methylammonium acetylhydrazide chloride or Pyr- die Cyangruppe steht, in alkoholischen Lösungs- 50 idinium - acetylhydrazidchlorid zur Umsetzung mitteln und in Gegenwart von Säuren mit Tri- bringt.the cyano group is in alcoholic solution 50 idinium - acetylhydrazide chloride for implementation and in the presence of acids with tri- brings. ® 309 728/281 10. 63® 309 728/281 10. 63
DEF35469A 1961-12-05 1961-12-05 Process for the preparation of acylhydrazones Pending DE1155773B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEF35469A DE1155773B (en) 1961-12-05 1961-12-05 Process for the preparation of acylhydrazones
GB4597962A GB1016654A (en) 1961-12-05 1962-12-05 New acyl-hydrazones,a process for preparing them,and preparations containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF35469A DE1155773B (en) 1961-12-05 1961-12-05 Process for the preparation of acylhydrazones

Publications (1)

Publication Number Publication Date
DE1155773B true DE1155773B (en) 1963-10-17

Family

ID=7096013

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF35469A Pending DE1155773B (en) 1961-12-05 1961-12-05 Process for the preparation of acylhydrazones

Country Status (2)

Country Link
DE (1) DE1155773B (en)
GB (1) GB1016654A (en)

Also Published As

Publication number Publication date
GB1016654A (en) 1966-01-12

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