CH139072A - Process for the preparation of a condensation product of the benzodiazine series. - Google Patents
Process for the preparation of a condensation product of the benzodiazine series.Info
- Publication number
- CH139072A CH139072A CH139072DA CH139072A CH 139072 A CH139072 A CH 139072A CH 139072D A CH139072D A CH 139072DA CH 139072 A CH139072 A CH 139072A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzodiazine
- series
- condensation product
- preparation
- dyes
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 7
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical class N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GVRRXASZZAKBMN-UHFFFAOYSA-N 4-chloroquinazoline Chemical compound C1=CC=C2C(Cl)=NC=NC2=C1 GVRRXASZZAKBMN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes der Benzodiazinreihe. Es wurde gefunden, dass man neue wert volle Kondensationsprodukte der Benzodiazin- reihe erhält, wenn man im Diazinring nrono- halogensubstituierte Chinazoline, ihre Homo logen, Analogen und Substitutionsprodukte mit beliebigen substituierten oder unsubsti- tuierten Aminen, Phenolen oder solchen Ver bindungen kondensiert,
die an Schwefelatomen reaktionsfähige Wasserstoffatome besitzen. Man gelangt so zu neuen Produkten, die als solche oder nach weiteren Umwandlungen die verschiedenartigste Verwendung finden können, zum Beispiel als Zwischenprodukte für Farb stoffe und Pharmazeutika.
Gegenstand vorliegender Erfindung ist nun ein Verfahren zur Darstellung eines Kon densationsproduktes der Benzodiazinreihe von der Formel
EMI0001.0017
dadurch gekennzeichnet, dass man 4-Halogen- chinazolin mit 1-Amino-8-oxynaphtalin-3.6- disulfosäure kondensiert.
<I>Beispiel:</I> 16,4 Gewichtsteile gepulvertes 4-Chlor- chinazolin
EMI0001.0025
werden bei 40 in eine aus 34,1 Gewichts teilen des sauren Natriumsalzes der 1-Amino- 8-oxynaphtaliir-3.6-disulfosäure, 700 Teilen Wasser und 13,6 Gewichtsteilen kristallisier tem Natriumacetat hergestellte Lösung unter gutem Rühren langsam eingetragen. Die Kondensation setzt sofort unter Gelbfärbung der Lösung ein; ein Teil des Kondensations produktes fällt aus. Wenn die Reaktions komponenten verschwunden sind, salzt mal] aus.
Das Kondensationsprodukt, dem die Formel
EMI0002.0001
zukommt, ist nach der üblichem Aufarbeitung ein gelbes, als Natriumsalz in Wasser gut lösliches kristallines Pulver; seine alkalischen Lösungen fluoreszieren nicht. Die neue Ver bindung reagiert nicht mit salpetriger Säure. Sie soll als Zwischenprodukt für die Her stellung von Farbstoffen und Arzneimitteln dienen.
Process for the preparation of a condensation product of the benzodiazine series. It has been found that new valuable condensation products of the benzodiazine series are obtained if nronohalogen-substituted quinazolines, their homologues, analogues and substitution products are condensed with any substituted or unsubstituted amines, phenols or such compounds in the diazine ring,
which have hydrogen atoms capable of reacting with sulfur atoms. This leads to new products which, as such or after further transformations, can be used in a wide variety of ways, for example as intermediates for dyes and pharmaceuticals.
The present invention is a process for the preparation of a condensation product of the benzodiazine series of the formula
EMI0001.0017
characterized in that 4-haloquinazoline is condensed with 1-amino-8-oxynaphthalene-3.6-disulfonic acid.
<I> Example: </I> 16.4 parts by weight of powdered 4-chloro-quinazoline
EMI0001.0025
are slowly entered at 40 in a solution prepared from 34.1 parts by weight of the acidic sodium salt of 1-amino-8-oxynaphthalene-3,6-disulfonic acid, 700 parts of water and 13.6 parts by weight of crystallized sodium acetate with thorough stirring. The condensation starts immediately and the solution turns yellow; part of the condensation product falls out. When the reaction components have disappeared, salt out].
The condensation product that the formula
EMI0002.0001
is a yellow crystalline powder which is readily soluble in water as the sodium salt; its alkaline solutions do not fluoresce. The new compound does not react with nitrous acid. It should serve as an intermediate for the manufacture of dyes and drugs.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE139072X | 1927-02-03 | ||
| CH133192T | 1927-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139072A true CH139072A (en) | 1930-03-31 |
Family
ID=25711992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139072D CH139072A (en) | 1927-02-03 | 1928-01-30 | Process for the preparation of a condensation product of the benzodiazine series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139072A (en) |
-
1928
- 1928-01-30 CH CH139072D patent/CH139072A/en unknown
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