AT201596B - Process for the production of the new 3-cyano-phenthiazine - Google Patents
Process for the production of the new 3-cyano-phenthiazineInfo
- Publication number
- AT201596B AT201596B AT201596DA AT201596B AT 201596 B AT201596 B AT 201596B AT 201596D A AT201596D A AT 201596DA AT 201596 B AT201596 B AT 201596B
- Authority
- AT
- Austria
- Prior art keywords
- phenthiazine
- cyano
- new
- production
- cyanide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- DPUVPRWTWNQSOS-UHFFFAOYSA-N 3-chloro-10h-phenothiazine Chemical compound C1=CC=C2SC3=CC(Cl)=CC=C3NC2=C1 DPUVPRWTWNQSOS-UHFFFAOYSA-N 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung des neuen 3-Cyano-phenthiazins
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung des neuen 3-Cyanophenthiazins (Numerierung nach Beilstein) der Formel :
EMI1.1
Das der Formel (I) entsprechende Produkt kann durch Einwirkung eines Metallcyanids oder - ferrocyanids, wie beispielsweise Kupfercyanid, auf ein 3-Halogenphenthiazin, insbesondere auf das 3-Chlorphenthiazin, vorzugsweise in einem das Cyanid komplex bindenden Medium, wie beispielsweise Pyridin, Chinolin oder Benzonitril erhalten werden.
Das erfindungsgemäss erhaltene 3-Cyano-phenthiazin ist ein besonders wertvolles Zwischenprodukt bei der Herstellung von Produkten mit wertvollen pharmakodynamischen Eigenschaften.
Das folgende Beispiel erläutert die Erfindung, ohne sie zu beschränken.
Beispiel :
Man mischt 1 kg 3-Chlorphenthiazin und 0, 5 kg Kupfer (I)-cyanid in fein verteilter Form, 10 g Kupferpulver und 1 g Jod in 1, 821 Chinolin.
Eventuell vorhandene Spuren von Wasser entfernt man durch Abdestillieren von ein wenig Chinolin und erhitzt dann 48 Stunden zum Rückfluss bei einer Temperatur von etwa 2500 C.
Nach Abkühlen auf 190 C giesst man die Reaktionsmasse in 271 etwa 3, 5n-Schwefelsäure. Es bildet sich ein braunschwarzer Niederschlag, den man abfiltriert, mit Wasser wäscht und trocknet.
Dieses Rohprodukt zieht man mit 91 siedendem Isopropyläther aus. Aus der Mutterlauge scheidet sich eine erste Fraktion an 3-Cyano-phenthiazin ab. Man behandelt den unlöslichen Anteil mit einer siedenden wässerigen Kaliumcyanidlösung, wäscht den Rückstand mit verdünnter Schwefelsäure und mit Wasser, trocknet ihn und zieht ihn erneut mit Isopropyläther aus. Man isoliert so eine zweite 3-Cyanophenthiazin-Fraktion und erhält schliesslich insgesamt 580 g 3-Cyanophenthiazin in Form eines gelben kristallinen Pulvers vom F = 2040 C (Kofler- ank).
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of the new 3-cyano-phenthiazine
The present invention relates to a process for the preparation of the new 3-cyanophenthiazine (numbering according to Beilstein) of the formula:
EMI1.1
The product corresponding to the formula (I) can be produced by the action of a metal cyanide or metal ferrocyanide, such as copper cyanide, on a 3-halophenthiazine, in particular on 3-chlorophenthiazine, preferably in a medium that binds the cyanide complex, such as pyridine, quinoline or benzonitrile can be obtained.
The 3-cyano-phenthiazine obtained according to the invention is a particularly valuable intermediate in the production of products with valuable pharmacodynamic properties.
The following example explains the invention without restricting it.
Example:
Mix 1 kg of 3-chlorophenthiazine and 0.5 kg of copper (I) cyanide in finely divided form, 10 g of copper powder and 1 g of iodine in 1.821 quinoline.
Any traces of water that may be present are removed by distilling off a little quinoline and then refluxing for 48 hours at a temperature of about 2500 C.
After cooling to 190 ° C., the reaction mass is poured into about 3.5N sulfuric acid. A brown-black precipitate forms, which is filtered off, washed with water and dried.
This crude product is extracted with 91 boiling isopropyl ether. A first fraction of 3-cyano-phenthiazine separates from the mother liquor. The insoluble fraction is treated with a boiling aqueous potassium cyanide solution, the residue is washed with dilute sulfuric acid and with water, dried and extracted again with isopropyl ether. A second 3-cyanophenthiazine fraction is isolated in this way and finally a total of 580 g of 3-cyanophenthiazine is obtained in the form of a yellow crystalline powder with a melting point of 2040 ° C. (Kofler ank).
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR201596X | 1957-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT201596B true AT201596B (en) | 1959-01-10 |
Family
ID=8880028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT201596D AT201596B (en) | 1957-03-07 | 1958-01-03 | Process for the production of the new 3-cyano-phenthiazine |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT201596B (en) |
-
1958
- 1958-01-03 AT AT201596D patent/AT201596B/en active
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