CH265709A - Process for the preparation of a derivative of 4-methyl-7-benzylamino-coumarin. - Google Patents

Process for the preparation of a derivative of 4-methyl-7-benzylamino-coumarin.

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Publication number
CH265709A
CH265709A CH265709DA CH265709A CH 265709 A CH265709 A CH 265709A CH 265709D A CH265709D A CH 265709DA CH 265709 A CH265709 A CH 265709A
Authority
CH
Switzerland
Prior art keywords
benzylamino
coumarin
methyl
derivative
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH265709A publication Critical patent/CH265709A/en

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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
    • C07D311/06—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
    • C07D311/16—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 7

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines Derivats des     4-Methyl-7-benzylamino-cumarins.       Es wurde gefunden, dass man zu einem  Derivat des     4-Methyl-7-benzylamino-cumarins     gelangt, wenn man     4-Met.hyl-7-benzylamino-          cumarin    durch Behandeln mit einem     Sulfo-          nierungsmittel    in eine     Monosulfonsäure    über  führt.  



  Als     Sulfonierung4inittel    kann man bei  spielsweise konzentrierte     Sehwefelsäure    oder       Schwefelsäuremonohy        drat    verwenden. Die       Sulfonierung    wird vorteilhaft bei etwa 70 bis  75  C vorgenommen.  



  Das     Natriumsalz    der neuen     Sulfonsäure     bildet, ein helles Pulver, das von Wasser zu  einer     bläulieh    fluoreszierenden Lösung auf  genommen wird. Es kann     zum    optischen  Bleicher von Wolle verwendet werden.  



  <I>Beispiel:</I>  35 Teile     4-Methyl-7-aniino-cumarin    wer  den mit 12 Teilen     Benzy        lchlorid    und 400  Teilen     Äthylalkohol    24 Stunden rückfliessend  gekocht. Nach dem Erkalten wird filtriert,  der Rückstand mit Alkohol gewaschen, dann  mit 5%iger     Salzsäure    verrührt,     uni    den Aus  gangsstoff zu entfernen, -.filtriert, mit Wasser  gewaschen, getrocknet und aus Alkohol kri  stallisiert.  



  Man erhält helle Kristalle, die in Wasser  unlöslich sind.  



  5 Teile der so erhaltenen Verbindung  werden in 30 Teilen Monohydrat gelöst  und bei 70-75 C verrührt., bis eine Probe    in verdünnter     Natriumcarbonatlösiuig    löslich  geworden ist. Man kühlt dann ab, giesst  auf Eis, neutralisiert mit Natronlauge und  dampft im Vakuum bei 60-80 C zur       Trockne    ein. Das erhaltene Pulver wird mit  heissem Methanol ausgezogen und der Auszug       zur    Trockne eingedampft.  



  Man erhält ein helles Pulver, das in       Wasser        lösliefi    ist. Die     Lösung    fluoresziert  bläulich.



  Process for the preparation of a derivative of 4-methyl-7-benzylamino-coumarin. It has been found that a derivative of 4-methyl-7-benzylamino-coumarin is obtained if 4-methyl-7-benzylaminocoumarin is converted into a monosulphonic acid by treatment with a sulphonating agent.



  Concentrated sulfuric acid or sulfuric acid monohydrate, for example, can be used as the sulfonation agent. The sulfonation is advantageously carried out at about 70 to 75.degree.



  The sodium salt of the new sulfonic acid forms, a light-colored powder that is absorbed by water to form a bluish fluorescent solution. It can be used for optical bleaching of wool.



  <I> Example: </I> 35 parts of 4-methyl-7-aniino-coumarin are refluxed for 24 hours with 12 parts of benzyl chloride and 400 parts of ethyl alcohol. After cooling, it is filtered, the residue is washed with alcohol, then stirred with 5% hydrochloric acid, uni to remove the starting material, -.filtered, washed with water, dried and crystallized from alcohol.



  Light-colored crystals are obtained which are insoluble in water.



  5 parts of the compound thus obtained are dissolved in 30 parts of monohydrate and stirred at 70-75 ° C. until a sample has become soluble in dilute sodium carbonate solution. It is then cooled, poured onto ice, neutralized with sodium hydroxide solution and evaporated to dryness in vacuo at 60-80 ° C. The powder obtained is extracted with hot methanol and the extract is evaporated to dryness.



  A light-colored powder is obtained which is soluble in water. The solution has a bluish fluorescence.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Derivats des 4-llethyl-7-benzylamino-euma- rins, dadurch gekennzeichnet, dass man 4-llethyl-7-benzylamino-cumarin durch Be handeln mit. einem Sulfonierungsmittel in eine llonosulfonsäure überführt. Das Natriumsalz der neuen Sulfonsäure bildet, ein helles Pulver, das von Wasser zu einer bläulich fluoreszierenden Lösung auf genommen wird. Es kann zum optischen Bleichen von Wolle verwendet werden.. <B>UNTER-ANSPRÜCHE:</B> 1. PATENT CLAIM: Process for the preparation of a new derivative of 4-llethyl-7-benzylamino-eumarin, characterized in that 4-llethyl-7-benzylamino-coumarin is treated with. converted into an ionosulfonic acid using a sulfonating agent. The sodium salt of the new sulfonic acid forms, a light-colored powder that is taken up by water to form a bluish fluorescent solution. It can be used for the optical bleaching of wool. <B> SUB-CLAIMS: </B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als Sulfonie- rungsmittel Schw efelsäuremonohy drat ver wendet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet., dass man Schwefelsäuremonohi#drat bei 70 bis 75 C einwirken lässt. Process according to patent claim, characterized in that sulfuric acid monohydrate is used as the sulfonating agent. 2. The method according to claim and dependent claim 1, characterized. That sulfuric acid monohydrate is allowed to act at 70 to 75 C.
CH265709D 1946-06-14 1946-06-14 Process for the preparation of a derivative of 4-methyl-7-benzylamino-coumarin. CH265709A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH265709T 1946-06-14
CH260835T 1946-06-14

Publications (1)

Publication Number Publication Date
CH265709A true CH265709A (en) 1949-12-15

Family

ID=25730335

Family Applications (1)

Application Number Title Priority Date Filing Date
CH265709D CH265709A (en) 1946-06-14 1946-06-14 Process for the preparation of a derivative of 4-methyl-7-benzylamino-coumarin.

Country Status (1)

Country Link
CH (1) CH265709A (en)

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