CH106124A - Process for the preparation of 4-chloro-1,2-thionaphthisatin. - Google Patents
Process for the preparation of 4-chloro-1,2-thionaphthisatin.Info
- Publication number
- CH106124A CH106124A CH106124DA CH106124A CH 106124 A CH106124 A CH 106124A CH 106124D A CH106124D A CH 106124DA CH 106124 A CH106124 A CH 106124A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- thionaphthisatin
- preparation
- parts
- halogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung des 4-Clilor-1,2-thionaphtliisatins. Es wurde gefunden, dass man zu dem 4-Chlor-l,2-thionaphthisatin gelangen kann, wenn man im 4-Chlor-1,2-naphththioindoxyl, durch Behandeln mit Halogen, die Wasser stoffatome der Methylengruppe durch Ha logen substituiert und hierauf die so er haltenen Produkte mit verseifenden Mitteln, wie anorganischen oder organischen Säuren, behandelt, wobei die angelagerten Halogene als Igalogen-%,%,asserstoffsäuren abgespalten werden.
<I>Beispiel</I> 234,5 Teile 4-Chlor-1,2-naphththioiniioxyl werden bei 30 bis 35 in 2500 Teilen Eis essig suspendiert. Bei dieser Temperatur gibt man unter E.ühren eine Lösung von 820 Teilen Brom in 500 Teilen Eisassig zu. Es entsteht eine braune Lösung; aus der sieh bald ein gelbbrauner Niederschlag abzu- scheiden beginnt:. Nach kurzem Rühren ist das Brom verschwunden.
Nach dem Filtrie ren und Umkristallisieren des Niederschlages aus heissem Eisessig erhält man das 2-1.)i- bromid des 4-Cfilor-1,2-thionaphtliisatins in W guter Ausbeute als gelbe Kristalle vom Schmelzpunkt 178 .
392,5 Teile 2-Dibromid des 4-Chlor-.1,2- thionaphthisatixis werden nun in 7000 Teilen 85 %iger Schwefelsäure suspendiert und un ter Rühren auf 110 erhitzt.
Unter Broin- wasserstoffabspaltung geht der Körper mit braunroter Farbe in Lösung, und bzild be ginnt die Abscheidung des 4-Chlor-1,2-t.liio- naphtliisatins. Zur Vervollständigung- der Bromwasserstoffabspaltung wird einige Zeit auf 120 bis 130 belassen, dann mit Wasser verdünnt, filtriert,
genraschen und getrocknet. Nach .dem Umlösen aus verdünnter Natron lauge und einmali(rem Umkrlstalllsleren alis Benzol wird das 4-Clilor-l.,2-thionaphtliisaiin in violettroten Nadeln voni Schmelzpunkt <B><U>920'</U></B> erhalten.
Process for the preparation of 4-Clilor-1,2-thionaphthiisatin. It has been found that the 4-chloro-l, 2-thionaphthisatin can be obtained if the hydrogen atoms of the methylene group are substituted by halogen in 4-chloro-1,2-naphththioindoxyl by treatment with halogen and then the Products obtained in this way are treated with saponifying agents such as inorganic or organic acids, with the accumulated halogens being split off as Igalogen -%,%, hydrogen acids.
<I> Example </I> 234.5 parts of 4-chloro-1,2-naphththioiniioxyl are suspended at 30 to 35 in 2500 parts of glacial acetic acid. At this temperature, a solution of 820 parts of bromine in 500 parts of glacial acetic acid is added while stirring. A brown solution results; from which a yellow-brown precipitate soon begins to separate :. The bromine has disappeared after a brief stir.
After filtration and recrystallization of the precipitate from hot glacial acetic acid, the 2-1.) I-bromide of 4-Cfilor-1,2-thionaphthiatisatin is obtained in good yield as yellow crystals with a melting point of 178.
392.5 parts of 2-dibromide des 4-chloro-1,2-thionaphthisatixis are now suspended in 7000 parts of 85% strength sulfuric acid and heated to 110 with stirring.
With splitting off of brine hydrogen, the body goes into solution with a brownish-red color, and the separation of 4-chloro-1,2-t.liionaphthiatisatin begins in bzild. To complete the elimination of hydrogen bromide, it is left at 120 to 130 for some time, then diluted with water, filtered,
piqued and dried. After redissolving from dilute sodium hydroxide solution and one-time liquid crystal as benzene, the 4-chloro-1,2-thionaphthylic acid is obtained in violet-red needles with a melting point of <B><U>920'</U> </B>.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH105234T | 1923-01-29 | ||
CH106124T | 1923-02-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH106124A true CH106124A (en) | 1924-08-01 |
Family
ID=25706819
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH106124D CH106124A (en) | 1923-01-29 | 1923-02-12 | Process for the preparation of 4-chloro-1,2-thionaphthisatin. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH106124A (en) |
-
1923
- 1923-02-12 CH CH106124D patent/CH106124A/en unknown
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