CH124080A - Process for the preparation of an organic rhodane compound. - Google Patents
Process for the preparation of an organic rhodane compound.Info
- Publication number
- CH124080A CH124080A CH124080DA CH124080A CH 124080 A CH124080 A CH 124080A CH 124080D A CH124080D A CH 124080DA CH 124080 A CH124080 A CH 124080A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- organic
- rhodan
- compound
- rhodane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003929 acidic solution Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical group NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer organischen Rhodanverbindung. Im Hauptpatent ist ein Verfahren zur Einführung von Rhodangruppen in organische Verbindungen beschrieben, nach welchem man auf die zu rhodanierende organische Verbindung ein anorganisches Rhodanid in gelöster Form und gleichzeitig ein Halogen zur Einwirkung bringt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung des 1-Rhodan- 2-naphtylamins der Formel
EMI0001.0007
welches dadurch gekennzeichnet ist, dass man ein anorganisches Rhodanid in gelöster Form und gleichzeitig ein Halogen auf ss-Naphtyl- amin einwirken lässt.
Das so erhaltene 1-Rhodan-2-naphtylamin ist in organischen Lösungsmitteln löslich und kann aus Alkohol, Benzol oder Tetrachlor- kohlenstoff umkristallisiert werden. Es sintert bei 150-154o und schmilzt bei etwa 2610 unter vollständiger Zersetzung.
Es soll als Zwischenprodukt zur Herstellung von Farb stoffen und pharmazeutischen Produkten Ver wendung finden. <I>Beispiel:</I> Eine Lösung von 71 Teilen R-Naphtyl- amin in 450 Teilen Essigsäure (96 %) wird zu einer Lösung von 160 Teilen Rhodan- natrium in 1200 Teilen Essigsäure gegeben.
Zu der Mischung, in der sich das rhodan- wasserstoffsaure Salz des f-Naphtylamins teilweise abscheidet, werden 80 Teile Brom, gelöst in 350 Teilen Essigsäure, unter Kühlen zugetropft. Während des Bromzusatzes ver schwindet der Niederschlag und die Lösung wird klar. Wenn die ganze Menge Brom zu gelaufen ist; entsteht nach einiger Zeit ein neuer Niederschlag, der filtriert und mit Sodalösung gewaschen wird. Auf diese Weise erhält man das bisher unbekannte 1-Rhodan- 2-naphtylamin.
Process for the preparation of an organic rhodane compound. The main patent describes a process for introducing rhodan groups into organic compounds, according to which an inorganic rhodanide in dissolved form and at the same time a halogen are brought into action on the organic compound to be rhodanized.
The present patent relates to a process for the preparation of 1-rhodan-2-naphthylamine of the formula
EMI0001.0007
which is characterized in that an inorganic rhodanide in dissolved form and at the same time a halogen are allowed to act on ß-naphthylamine.
The 1-rhodan-2-naphthylamine obtained in this way is soluble in organic solvents and can be recrystallized from alcohol, benzene or carbon tetrachloride. It sinters at 150-154o and melts at about 2610 with complete decomposition.
It is intended to be used as an intermediate product in the manufacture of dyes and pharmaceutical products. <I> Example: </I> A solution of 71 parts of R-naphthylamine in 450 parts of acetic acid (96%) is added to a solution of 160 parts of sodium rhodan in 1200 parts of acetic acid.
80 parts of bromine, dissolved in 350 parts of acetic acid, are added dropwise with cooling to the mixture in which the rhodanhydrous acid salt of f-naphthylamine is partially deposited. During the addition of bromine, the precipitate disappears and the solution becomes clear. When all the bromine has run out; After a while, a new precipitate is formed, which is filtered and washed with soda solution. In this way, the previously unknown 1-rhodan-2-naphthylamine is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE124080X | 1925-08-27 | ||
| CH122990T | 1926-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH124080A true CH124080A (en) | 1928-01-02 |
Family
ID=25709979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH124080D CH124080A (en) | 1925-08-27 | 1926-08-13 | Process for the preparation of an organic rhodane compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH124080A (en) |
-
1926
- 1926-08-13 CH CH124080D patent/CH124080A/en unknown
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