CH106121A - Process for the preparation of the 2,1 thionaphthisatin. - Google Patents
Process for the preparation of the 2,1 thionaphthisatin.Info
- Publication number
- CH106121A CH106121A CH106121DA CH106121A CH 106121 A CH106121 A CH 106121A CH 106121D A CH106121D A CH 106121DA CH 106121 A CH106121 A CH 106121A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- thionaphthisatin
- parts
- halogen
- acetic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung des 2,1 Thionaphthisatins. <B>Es</B> wurde gefunden, dass man zu dem 2,1-Thionaplithisatin gelangen kann, wenn man im 2,1-Naphththioindoxyl, durch Behan deln mit Halogen, die Wasserstoffatome der Methylengruppe durch Halogen substituiert und hierauf die so erhaltenen Produkte mit verseifenden Mitteln, -wie anorganischen oder organischen Säuren, behandelt, ,wobei die angelagerten Halogene als Halogenwasser stoffsäuren abgespalten werden.
Beispiel: 200 Teile 2,1.-Naphththioindoxyl werden in 2400 Teilen Eisessig bei 25 bis 30 gelöst. Bei dieser Temperatur gibt man unter Rüh ren eine Lösung von 320 Teilen Broin in <B>500</B> Teilen Eisessig zu. Es scheidet sich ein brauner, kristalliner Niederschlag ab und nach kurzem Rühren ist das Brom ver schwunden.
Nach dem Filtrieren und Uni- kristallisieren des Niederschlages aus heissem Eisessig erhält man das 2-Dibromid des 2,1- Thionaphthisatins in guter Ausbeute als gelle Kristalle vom Schmelzpunkt 150 . 358 Teile 2-Dibromid des 2,1-T'hio- naphthisatins werden nun in 9000 Teile 40 obige Essigsäure unter Rühren eingetragen und das Gemisch zum Sieden erhitzt. Unter Bromwasserstoffabspaltung entsteht eine rötlichgelbe Lösung. Nach kurzem Sieden ist die Reaktion zu Ende.
Die Lösung wird heiss filtriert; aus dein Filtrat scheidet sich das 2,1-Naphththioisatin als orangerote Kri stalle in sehr guter Ausbeute ab.
Process for the preparation of the 2,1 thionaphthisatin. It has been found that the 2,1-thionaplithisatin can be obtained if, in 2,1-naphththioindoxyl, by treating with halogen, the hydrogen atoms of the methylene group are substituted by halogen and then the hydrogen atoms thus obtained Products treated with saponifying agents, such as inorganic or organic acids, with the accumulated halogens being split off as hydrogen halide acids.
Example: 200 parts of 2,1-naphththioindoxyl are dissolved in 2400 parts of glacial acetic acid at 25-30. At this temperature, a solution of 320 parts of broin in 500 parts of glacial acetic acid is added with stirring. A brown, crystalline precipitate separates out and after brief stirring the bromine has disappeared.
After filtering and unicrystallizing the precipitate from hot glacial acetic acid, the 2-dibromide of 2,1-thionaphthisatin is obtained in good yield as yellow crystals with a melting point of 150. 358 parts of 2-dibromide of 2,1-thio-naphthisatins are then introduced into 9000 parts of the above acetic acid with stirring and the mixture is heated to the boil. A reddish-yellow solution is formed with the elimination of hydrogen bromide. The reaction is over after a short boil.
The solution is filtered hot; the 2,1-naphthioisatin separates out of your filtrate as orange-red crystals in very good yield.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH106121T | 1923-01-29 | ||
| CH105234T | 1923-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH106121A true CH106121A (en) | 1924-08-01 |
Family
ID=25706817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH106121D CH106121A (en) | 1923-01-29 | 1923-01-29 | Process for the preparation of the 2,1 thionaphthisatin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH106121A (en) |
-
1923
- 1923-01-29 CH CH106121D patent/CH106121A/en unknown
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