CH216306A - Process for the preparation of a new derivative of a heterocyclic compound. - Google Patents
Process for the preparation of a new derivative of a heterocyclic compound.Info
- Publication number
- CH216306A CH216306A CH216306DA CH216306A CH 216306 A CH216306 A CH 216306A CH 216306D A CH216306D A CH 216306DA CH 216306 A CH216306 A CH 216306A
- Authority
- CH
- Switzerland
- Prior art keywords
- heterocyclic compound
- preparation
- product
- new derivative
- reaction
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 3
- 244000060011 Cocos nucifera Species 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000006277 sulfonation reaction Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Derivates einer heterocyelischen Verbindung. Es wurde gefunden, dass man zu einem neuen Derivat einer heterocyclischen Verbin dung gelangt, wenn man das Natriumsalz des sulfonierten Benzimidazols, das durch Kondensation von o-Phenylendiamin mit Kokosfettsäure und nachfolgende Sulfonie- rung erhalten wird, mit 1Vlonochloressigsäure- äthylester umsetzt,
auf das so erhaltene Re aktionsprodukt Diäthylanolamin einwirken lässt und das entstandene Umsetzungspro- dukt mit einer wässerigen Natriumhydrogyd- lösung behandelt.
Die Umsetzung mit dem Monochloressig- säureäthylester wind zweckmässig in der Wärme, vorteilhaft in Gegenwart eines Lö sungsmittels, vorgenommen.
Das "so erhaltene Produkt bildet nach dem Trocknen ein hellgefärbtes Pulver, .dessen wässerige Lösungen stark kapillaraktive Eigenschaften besitzen. Es kann als Tegtil- hilfsstoff verwendet werden.
<I>Beispiel:</I> 7 7 Gewichtsteile des Natriumsalzes des sulfonierten. Benzimidazols, das durch Kon densation von o-Phenylendiamin mit Kokos- fettsäure und nachfolgende Sulfonierung er halten wird,
und 26 Gewichtsteile Monochlor- essigsäureäthylester werden unter Rühren in 300 Volumteile Benzol eingetragen und die Mischung während 70 Stunden am Rückfluss- kühler auf Siedetemperatur erhitzt. Zum dünnflüssigen Reaktionsprodukt fügt man nun 22 Gewichtsteile Diäthanolamin und setzt das Erhitzen während weiteren 12 .Stun den fort.
Aus der resultierenden zähflüssigen Reaktionsmasse wird das Benzol unter ver- mindertem Druck abdestilliert. Der zurück bleibende, dunkelgefärbte und harzartige Rückstand ist in Wasser löslich, scheidet sich jedoch schon auf Zusatz einer geringen Säuremenge aus.
Man erhält ein in saurer Lösung bestän diges Produkt, indem man das Reaktionspro- dukt in warmem Wasser aufnimmt und nach Zusatz von 25 Gewichtsteilen 30 % iger Na triumhydroxydlösung kurz aufkocht. Aus der mit verdünnter Schwefelsäure neutralisierten Lösung erhält man durch Eindampfen ein hellgefärbtes Pulver, dessen wässerige Lö sungen stark kapillaraktive Eigenschaften besitzen.
Process for the preparation of a new derivative of a heterocyclic compound. It has been found that a new derivative of a heterocyclic compound is obtained if the sodium salt of sulfonated benzimidazole, which is obtained by condensation of o-phenylenediamine with coconut fatty acid and subsequent sulfonation, is reacted with ethyl monochloroacetate,
allows diethylanolamine to act on the reaction product obtained in this way and treats the resulting reaction product with an aqueous sodium hydrogen solution.
The reaction with the ethyl monochloroacetate is expediently carried out in the heat, advantageously in the presence of a solvent.
After drying, the product obtained in this way forms a light-colored powder, the aqueous solutions of which have strong capillary-active properties. It can be used as a Tegtil auxiliary.
<I> Example: </I> 7 7 parts by weight of the sodium salt of the sulfonated. Benzimidazole, which is obtained by condensation of o-phenylenediamine with coconut fatty acid and subsequent sulfonation,
and 26 parts by weight of ethyl monochloroacetate are introduced into 300 parts by volume of benzene with stirring and the mixture is heated to boiling temperature for 70 hours on a reflux condenser. 22 parts by weight of diethanolamine are now added to the low-viscosity reaction product and heating is continued for a further 12 hours.
The benzene is distilled off from the resulting viscous reaction mass under reduced pressure. The dark-colored, resin-like residue that remains is soluble in water, but separates out after only a small amount of acid is added.
A product which is stable in acidic solution is obtained by taking up the reaction product in warm water and, after adding 25 parts by weight of 30% sodium hydroxide solution, briefly boiling it. From the solution neutralized with dilute sulfuric acid, a light-colored powder is obtained by evaporation, the aqueous solutions of which have strong capillary-active properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH213253T | 1939-05-24 | ||
| CH216306T | 1939-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH216306A true CH216306A (en) | 1941-08-15 |
Family
ID=25725394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH216306D CH216306A (en) | 1939-05-24 | 1939-05-24 | Process for the preparation of a new derivative of a heterocyclic compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH216306A (en) |
-
1939
- 1939-05-24 CH CH216306D patent/CH216306A/en unknown
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