CH158240A - Process for the preparation of 2,1-naphthioindoxyl-4-carboxylic acid. - Google Patents

Process for the preparation of 2,1-naphthioindoxyl-4-carboxylic acid.

Info

Publication number
CH158240A
CH158240A CH158240DA CH158240A CH 158240 A CH158240 A CH 158240A CH 158240D A CH158240D A CH 158240DA CH 158240 A CH158240 A CH 158240A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
acid
naphthioindoxyl
preparation
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH158240A publication Critical patent/CH158240A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/74—Naphthothiophenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Description

  

      Verfahren    zur Herstellung von     2,1-Naphththioindogyl-4-karbonsäure.       Es wurde gefunden, dass man die     2,1-          Naphththioindoxyl    - 4     -karbonsäure    herstellen  kann, wenn man die     2-Merkaptonaphthalin-4-          karbonsäure    mit     Monohalogenessigsäure    zu  der     3-Naphthyltbioglykol-l-karbonsäure    kon  densiert und diese hierauf mit ringschliessen  den Mitteln behandelt.  



  Die erhaltene     2,1-Naphththioindoxyl-4-ka.r-          bonsäure    der Formel  
EMI0001.0012     
    stellt ein schwach grüngefärbtes Pulver dar,  das- bei 230   noch nicht schmilzt und zur  Herstellung von Farbstoffen verwendet wer  den soll.  



       Beispiel:     20,4 Teile     2-Merkä.ptonaphthalin-4-kar-          bonsäure,    hergestellt aus 1-Amirronaphthalin-         3-sulfonsäure    durch Überführen in die     1-          Cyannaphthalin    - 3 -     sulfosäure,    Umwandlung  dieser letzteren in das     1-Cyannaphthalin-3-          sulfochlorid    und Reduktion dieses Pro  duktes; wobei zugleich die     Cyangruppe     verseift wird, werden in 200 Teilen Was  ser unter Beigabe von Soda alkalisch ge  löst;

   dazu gibt man eine sofiaalkalische Lö  sung von 10,4 Teilen Chloressigsäure und  erwärmt unter Rühren auf<B>800.</B> Hierauf wird  erkalten gelassen und die gebildete     3-Naph-          thylthioglykol-l-karbonsäur-e    durch     Ansäuern,     Filtrieren, Waschen und Trocknen gewonnen.  



  26,2 Teile dieses Körpers werden mit 31  Teilen     Phosphortrichlorid    in 60 Teilen     o-Di-          chlorbenzol    während drei Stunden auf dem  Wasserbade erhitzt; hierauf gibt man 14,8  Teile Aluminiumchlorid zu und rührt längere  Zeit bei     15-250.    Nach dem Austragen des  Reaktionsgemisches in Wasser und darauf  folgender     Wasserdampfdestillation,    wobei das       o-Dichlorbenzol    entfernt wird, erhält man die       2,1-Naphththioindoxyl-4-karbonsäure.         Zu demselben Produkt gelangt man, wenn  die in diesem Beispiel verwendete     Ohloressig-          säure    durch Bromessigsäure ersetzt wird,

   oder  wenn als ringschliessendes Mittel statt     Phos-          phortrichlorid    und Aluminiumchlorid     Schwe-          felsäuremonohydrat    oder     Chlorsulfonsäure    ver  wendet wird.



      Process for the production of 2,1-naphthioindogyl-4-carboxylic acid. It has been found that the 2,1-naphththioindoxyl-4-carboxylic acid can be produced if the 2-mercaptonaphthalene-4-carboxylic acid is condensed with monohaloacetic acid to form the 3-naphthyltbioglycol-1-carboxylic acid and this is then treated with ring-closing agents .



  The resulting 2,1-naphththioindoxyl-4-ka.rboxylic acid of the formula
EMI0001.0012
    represents a pale green colored powder that does not yet melt at 230 and is to be used for the production of dyes.



       Example: 20.4 parts of 2-Merkä.ptonaphthalin-4-carboxylic acid, prepared from 1-amirronaphthalene-3-sulfonic acid by converting it into 1-cyannaphthalene-3-sulfonic acid, converting this latter into 1-cyannaphthalene-3- sulfochloride and reduction of this product; at the same time the cyano group is saponified, in 200 parts of what water with the addition of soda alkaline ge dissolved;

   a sofiaalkaline solution of 10.4 parts of chloroacetic acid is added and heated to <B> 800 with stirring. </B> It is then allowed to cool and the 3-naphthylthioglycol-1-carboxylic acid formed is acidified, filtered, Washing and drying won.



  26.2 parts of this body are heated with 31 parts of phosphorus trichloride in 60 parts of o-dichlorobenzene for three hours on a water bath; 14.8 parts of aluminum chloride are then added and the mixture is stirred for a long time at 15-250. After discharging the reaction mixture into water and subsequent steam distillation, with the o-dichlorobenzene being removed, the 2,1-naphththioindoxyl-4-carboxylic acid is obtained. The same product is obtained if the chloroacetic acid used in this example is replaced by bromoacetic acid,

   or if sulfuric acid monohydrate or chlorosulfonic acid is used as a ring-closing agent instead of phosphorus trichloride and aluminum chloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 2,1-Naphth- thioindogyl-4-karbonsäure, dadurch gekenn zeichnet, dass man die 2-Merkaptonaphthalin- 4-karboiisäure mit Monohalogenessigsäure zu der 3-Naphthylthioglykol-l-karbonsäure kon densiert und diese hierauf mit ringscbliessen- den Mitteln behandelt. PATENT CLAIM: Process for the production of 2,1-naphthioindoglycol-4-carboxylic acid, characterized in that 2-mercaptonaphthalene-4-carbonic acid is condensed with monohaloacetic acid to form 3-naphthylthioglycol-1-carboxylic acid and this is then condensed with rings - Treated the means. Die erhaltene 2,1-Naphththioindogyl-4-kar- bonsäure der Formel: EMI0002.0018 stellt ein schwach grüngefärbtes Pulver dar, das bei<B>2300</B> noch nicht schmilzt und zur Herstellung von Farbstoffen verwendet wer den soll. The obtained 2,1-naphthioindogyl-4-carboxylic acid of the formula: EMI0002.0018 is a pale green colored powder that does not yet melt at <B> 2300 </B> and is intended to be used for the production of dyes.
CH158240D 1931-11-28 1931-11-28 Process for the preparation of 2,1-naphthioindoxyl-4-carboxylic acid. CH158240A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH158240T 1931-11-28

Publications (1)

Publication Number Publication Date
CH158240A true CH158240A (en) 1932-11-15

Family

ID=4412252

Family Applications (1)

Application Number Title Priority Date Filing Date
CH158240D CH158240A (en) 1931-11-28 1931-11-28 Process for the preparation of 2,1-naphthioindoxyl-4-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH158240A (en)

Similar Documents

Publication Publication Date Title
CH158240A (en) Process for the preparation of 2,1-naphthioindoxyl-4-carboxylic acid.
AT128350B (en) Process for the preparation of low-electrolyte aqueous solutions of silk fibroin.
AT106981B (en) Process for the production of acid-free, pure, resinous condensation products from phenols and aldehydes.
CH122588A (en) Process for the preparation of condensation products of the aromatic series.
CH153718A (en) Process for the preparation of a vat dye.
CH136040A (en) Process for the preparation of a new dye intermediate.
CH257405A (en) Process for the production of a new vat dye.
CH264198A (en) Process for the production of a vat dye.
CH193926A (en) Process for the preparation of a new dioxypyrene.
CH189302A (en) Process for the production of a new textile auxiliary.
CH140911A (en) Process for the preparation of a condensation product of the benzanthrone series.
CH216586A (en) Process for the preparation of a nitrogen-containing condensation product of fluoranthene.
CH157526A (en) Process for the production of a new azo dye.
CH120257A (en) Process for the preparation of a new oxynaphthalene carboxylic acid.
CH128127A (en) Process for the preparation of Bz1-oxybenzanthrone.
CH105233A (en) Process for the preparation of a thioindoxyl derivative.
CH235463A (en) Process for the preparation of an azo dye.
CH198146A (en) Process for the preparation of a dimethyl coeroxene.
CH187421A (en) Process for the production of a new textile auxiliary.
CH175881A (en) Process for the preparation of a substantive copper-containing azo dye.
CH234961A (en) Process for the preparation of the leuco sulfuric acid ester of a vat dye.
CH168022A (en) Process for the production of a vat dye.
CH216593A (en) Process for the preparation of a nitrogen-containing condensation product of fluoranthene.
CH234960A (en) Process for the preparation of the leuco sulfuric acid ester of a vat dye.
CH107339A (en) Process for the production of a vat dye.