DE1568954A1 - Process for the production of p-iodobenzalacetone, a new intermediate product for chemical synthesis, especially of pharmaceuticals - Google Patents

Process for the production of p-iodobenzalacetone, a new intermediate product for chemical synthesis, especially of pharmaceuticals

Info

Publication number
DE1568954A1
DE1568954A1 DE19661568954 DE1568954A DE1568954A1 DE 1568954 A1 DE1568954 A1 DE 1568954A1 DE 19661568954 DE19661568954 DE 19661568954 DE 1568954 A DE1568954 A DE 1568954A DE 1568954 A1 DE1568954 A1 DE 1568954A1
Authority
DE
Germany
Prior art keywords
pharmaceuticals
chemical synthesis
production
intermediate product
iodobenzalacetone
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
DE19661568954
Other languages
German (de)
Inventor
Kurt Binovic
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.)
Biosedra S A Lab
Original Assignee
Biosedra S A Lab
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 Biosedra S A Lab filed Critical Biosedra S A Lab
Publication of DE1568954A1 publication Critical patent/DE1568954A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
    • C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
    • C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C07C49/233—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C49/235—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

15639541563954

Laboratoires Biosedra S.A. in Malakoff/PrankreiohLaboratories Biosedra S.A. in Malakoff / Prankreioh

Verfahren zur Herstellung von p-Jod-benzolaoeton, ein neues Zwischenprodukt für die chemische Synthese, insbesondere vonProcess for the preparation of p-iodine-benzolaoeton, a new one Intermediate for chemical synthesis, especially of

PharmazeutikaPharmaceuticals

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von p-Jod-benzalaceton, ein neues Zwischenprodukt für die chemische Synthese, insbesondere von Pharmazeutika. The present invention relates to a process for the preparation of p-iodo-benzalacetone, a new intermediate product for chemical synthesis, especially of pharmaceuticals.

Das nach dem erfindungsgemäßen Verfahren hergestellte Zwischenprodukt ermöglicht die Synthese neuer in der Seitenkette kodierter Verbindungen, die als Pharmazeutika, Insbesondere als Antikoagulans Anwendung finden.The intermediate product produced by the process according to the invention enables the synthesis of new compounds encoded in the side chain which are used as pharmaceuticals, in particular as anticoagulants.

-2--2-

00 9815/1821 oricnaunspected00 9815/1821 oricnaunspected

Das erfindungsgemäße Verfahren zur Herstdlung von p-Jod-bezoJLaceton ist dadurch gekennzeichnet, daß p-Jodbezaldehyd mit Aceton in Gegenwart einer alkoholischen Lösung von Natriumhydroxyd bei Zimmertemperatur zum Reagieren gebracht wird.The process according to the invention for the preparation of p-iodo-benzaldehyde is characterized in that p-iodo-benzaldehyde is caused to react with acetone in the presence of an alcoholic solution of sodium hydroxide at room temperature.

Merkmale der nach dem erfindungsgeraäSen Verfahren hergestellten Verbindung:Features of the manufactured by the process according to the invention Link:

Strukturformel:Structural formula:

Empirische Formel: C10HqOJEmpirical formula: C 10 HqOJ

Molekulargewicht: 272 Aussehen: gelbliche Kristalle Schmelzpunkt: 105 bis 106° CMolecular weight: 272 Appearance: yellowish crystals. Melting point: 105 to 106 ° C

-3--3-

009815/1821009815/1821

Analyse:Analysis: BerechnetCalculated GefundenFound 4*,19 % 4 *, 19 % 44,08 % 44.08 % C % C % 3,31 % 3.31 % 3,35 % 3.35 % H ft H ft 46,69 % 46.69 % 47,00 % 47.00 % J %J% Beispiel:Example:

3 bis 4 g Ätznatron wurden mit 400 bis 600 com Aceton, 1,75 1 Alkohol und 2,30 1 Wasser vermischt. Anschließend wurde tropfenweise unter ständigem Rühren 3 Stunden lang bei Zimmertemperatur eine Lösung von 122 g p-Jodbenzaldehyd in 56o ecm absolutem Alkohol der Mischung zugefügt, danach wurde filtriert, der Niederschlag mit Wasser gewaschen und .unter Unterdruck getrocknet. Auf diese Weise wurde p-Jod-benzalaoeton mit einer Ausbeute von 60 bis 70 % gewonnen.3 to 4 g of caustic soda were mixed with 400 to 600 com acetone, 1.75 l alcohol and 2.30 l water. A solution of 122 g of p-iodobenzaldehyde in 56o ecm of absolute alcohol was then added dropwise to the mixture with constant stirring for 3 hours at room temperature, after which it was filtered, the precipitate was washed with water and dried under reduced pressure. In this way, p-iodo-benzalaoetone was obtained in a yield of 60 to 70 % .

PatentanspruchClaim

-4--4-

0-098 1 h/ 1 8210-098 1 h / 1 821

Claims (1)

PatentanspruchClaim Verfahren zur Herstellung von p-Jod-benzoJaceton, ein neues Zwistenprodukt der FormelProcess for the production of p-iodine-benzo-acetone, a new conflicting product of the formula ^ CH=CH-CO-CH3 ^ CH = CH-CO-CH 3 für die chemische Synthese, insbesondere von Pharmazeutika, dadurch gekennzeichnet, das p-Jodbenzaldehyd mit Aceton in Gegenwart einer alkoholischen Lösung von Natriumhydroxyd bei Zimmertemperatur zum Reagieren gebracht wird.for chemical synthesis, especially of pharmaceuticals, characterized in that p-iodobenzaldehyde reacted with acetone in the presence of an alcoholic solution of sodium hydroxide at room temperature will. P0QR1 S/1821P0QR1 S / 1821
DE19661568954 1966-03-18 1966-05-24 Process for the production of p-iodobenzalacetone, a new intermediate product for chemical synthesis, especially of pharmaceuticals Pending DE1568954A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR54094 1966-03-18

Publications (1)

Publication Number Publication Date
DE1568954A1 true DE1568954A1 (en) 1970-04-09

Family

ID=8604162

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19661568954 Pending DE1568954A1 (en) 1966-03-18 1966-05-24 Process for the production of p-iodobenzalacetone, a new intermediate product for chemical synthesis, especially of pharmaceuticals
DE19661543734 Pending DE1543734A1 (en) 1966-03-18 1966-05-24 Process for the preparation of pure [alpha- (p-iodo-phenyl) -1-acetyl-2-aethyl] -3-hydroxy-4-coumarin

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE19661543734 Pending DE1543734A1 (en) 1966-03-18 1966-05-24 Process for the preparation of pure [alpha- (p-iodo-phenyl) -1-acetyl-2-aethyl] -3-hydroxy-4-coumarin

Country Status (5)

Country Link
BE (1) BE679348A (en)
CH (1) CH452546A (en)
DE (2) DE1568954A1 (en)
ES (1) ES326449A1 (en)
GB (1) GB1073768A (en)

Also Published As

Publication number Publication date
GB1073768A (en) 1967-06-28
BE679348A (en) 1966-09-16
ES326449A1 (en) 1967-03-01
CH452546A (en) 1968-03-15
DE1543734A1 (en) 1969-08-21

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