DE613172C - Process for the preparation of condensation products of the oxazole series - Google Patents
Process for the preparation of condensation products of the oxazole seriesInfo
- Publication number
- DE613172C DE613172C DEI48209D DEI0048209D DE613172C DE 613172 C DE613172 C DE 613172C DE I48209 D DEI48209 D DE I48209D DE I0048209 D DEI0048209 D DE I0048209D DE 613172 C DE613172 C DE 613172C
- Authority
- DE
- Germany
- Prior art keywords
- condensation products
- preparation
- oxazole series
- series
- oxazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000007859 condensation product Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002916 oxazoles Chemical class 0.000 title claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- -1 aryl sulfinic acid salts Chemical class 0.000 description 2
- ZZMLJFHHPQXEQR-UHFFFAOYSA-N 1,3-benzoxazole-2-sulfonic acid Chemical compound C1=CC=C2OC(S(=O)(=O)O)=NC2=C1 ZZMLJFHHPQXEQR-UHFFFAOYSA-N 0.000 description 1
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Verfahren zur Darstellung von Kondensationsprodukten der Oxazolreihe Durch das Hauptpatent 6o9 o25 wird ein Verfahren zur Darstellung von neuen Kondensationsprodukten der Thiazolreihe geschützt, das darin besteht, daß man 2-Halogenarylenthiazolverbindungen mit Alkalisulfiten bzw. arylsulfinsauren Salzen umsetzt.Process for the preparation of condensation products of the oxazole series The main patent 6o9 o25 provides a process for the preparation of new condensation products the thiazole series, which consists in the fact that one 2-haloarylenethiazole compounds with alkali sulfites or aryl sulfinic acid salts.
In weiterer Ausbildung des Verfahrens wurde gefunden, daß, soweit es sich um die Umsetzung mit Alkalisulfiten handelt, auch Halogenverbindungen der Zusammensetzung geeignet sind und zu bisher unbekannten Kondensationsprodukten vom Typus von C-Sulfonsäuren führen, ohne daß überraschenderweise die Umsetzung in anderer Richtung verläuft.In a further development of the process it was found that, as far as the reaction with alkali metal sulfites is concerned, halogen compounds of the composition are also used are suitable and lead to previously unknown condensation products of the C-sulfonic acid type without, surprisingly, the reaction proceeding in the other direction.
Da die als Ausgangsstoffe dienenden 2-Halogenarylenoxazole, wie aus der Literatur bekannt, nach verschiedenen Verfahren leicht herzustellen sind, sind auch die nach vorliegendem Verfahren in glatter Umsetzung daraus erhältlichen Kondensationsprodukte leicht zugänglich. Sie sollen als Zwischenkörper zur Herstellung von Farbstoffen und Heilmitteln Verwendung finden. Beispiel 154 kg 2-Chlorbenzoxazol (Kp. 2o4 bis 2o5°) läßt man in eine neutrale Natriumsulfitlösung, hergestellt aus 480 kg Natriumbisulfitlösung 38' Be, 360 1 Wasser und 229 kg Natronlauge (spez. Gewicht I,43), einlaufen.Since the 2-haloaryleneoxazoles used as starting materials, as known from the literature, can be easily prepared by various processes, the condensation products obtainable therefrom in smooth conversion by the present process are also easily accessible. They should be used as intermediate bodies for the production of dyes and medicines. Example 154 kg of 2-chlorobenzoxazole (bp. 204 to 205 °) are allowed to run into a neutral sodium sulfite solution prepared from 480 kg of sodium bisulfite solution 38 ' Be, 360 1 of water and 229 kg of sodium hydroxide solution (specific weight 1.43).
Nach 12stündigem Kochen unter Rückfluß bei gutem Rühren ist die Umsetzung beendet, was sich durch das Verschwinden des Öles bemerkbar macht.After refluxing for 12 hours with thorough stirring, the reaction is complete ends, which is noticeable by the disappearance of the oil.
Beim Erkalten kristallisiert die Benzoxazola-sulfonsäure in Form ihres Natriumsalzes in derben farblosen Nadeln aus.When cooling down, the benzoxazol sulfonic acid crystallizes in its form Sodium salt in coarse, colorless needles.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48209D DE613172C (en) | 1933-10-28 | 1933-10-28 | Process for the preparation of condensation products of the oxazole series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48209D DE613172C (en) | 1933-10-28 | 1933-10-28 | Process for the preparation of condensation products of the oxazole series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE613172C true DE613172C (en) | 1935-05-13 |
Family
ID=7192197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48209D Expired DE613172C (en) | 1933-10-28 | 1933-10-28 | Process for the preparation of condensation products of the oxazole series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE613172C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284294A (en) * | 1964-04-29 | 1966-11-08 | Bayer Ag | Methods and compositions for treating soil |
-
1933
- 1933-10-28 DE DEI48209D patent/DE613172C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284294A (en) * | 1964-04-29 | 1966-11-08 | Bayer Ag | Methods and compositions for treating soil |
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