CH240109A - Process for the preparation of a new a, B-di- (benzimidazyl- (2)) - ethylene. - Google Patents
Process for the preparation of a new a, B-di- (benzimidazyl- (2)) - ethylene.Info
- Publication number
- CH240109A CH240109A CH240109DA CH240109A CH 240109 A CH240109 A CH 240109A CH 240109D A CH240109D A CH 240109DA CH 240109 A CH240109 A CH 240109A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- benzimidazyl
- ethylene
- phenylenediamine
- preparation
- Prior art date
Links
- 239000005977 Ethylene Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000007717 exclusion Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen a,ss-Bi-[benzimidazyl-(2)]-äthylens. 1';s wurde gefunden, dass man zu einem neuen a,ss-Di- [benzimidazyl-(2)] - äthylen ge langt, wenn man eine Verbindung von der Formel
EMI0001.0006
bei erhöhter Temperatur auf o-Phenylendiamin einwirken lässt.
Als Verbindungen von der Formel
EMI0001.0008
kommen Maleinsäure oder deren funktionelle Derivate, z. B. Ester, in Betracht.
Die Umsetzung des o - Phenylendiamins mit den angeführten Verbindungen wird, falls die Dicarbonsäure als Ausgangsstoff heran gezogen wird, zweckmässig bei 120 - 180 , vorteilhaft unter Ausschluss von Sauerstoff, vorgenommen. Das neue a,ss-Di-[benzimidazyl-(2)]-äthylen bildet ein nahezu farbloses Pulver, das in Wasser und in den üblichen organischen Lö sungsmitteln unlöslich bis schwerlöslich ist. Es wird von verdünnter heisser Salzsäure zu einer grünlichgelben Lösung aufgenommen. Es kann als Zwischenprodukt, z.
B. zur Her stellung von Textilhilfsstoffen, ferner als op tisches Bleichmittel Anwendung finden. Für den letztgenannten Zweck kommt auch das Dinatriumsalz des neuen Endstoffes in Frage. <I>Beispiel:</I> 660 Teile o-Phenylendiamin werden mit 116 Teilen Maleinsäure unter Ausschluss von Luft innerhalb 3-5 Stunden von 120 auf 160 erhitzt. Sobald die Wasserabspaltung nachlässt, steigert man die Temperatur bis gegen 190 und hält noch kurze Zeit bei 190-195 , bis kein Wasser mehr entweicht. Man lässt abkühlen und entfernt das über schüssige o-Phenylendiamin durch Ausziehen mit Alkohol, Benzol oder einem andern Lö sungsmittel.
Der Rückstand wird in heisser, verdünnter Salzsäure gelöst und das Konden sationsprodukt aus der Lösung mit einem al kalischen Mittel, z. B. mit Ammoniak, aus gefällt, abfiltriert und mit Wasser neutral gewaschen. Es kann über das Hydrochlorid weiter gereinigt werden.
Das neue Produkt bildet ein nahezu farb loses Pulver, das in Wasser und in den üb lichen organischen Lösungsmitteln unlöslich bis schwerlöslich ist. Es wird von verdünn ter, heisser Salzsäure zu einer grünlichgelben Lösung aufgenommen.
Process for the preparation of a new a, ss-bi- [benzimidazyl- (2)] - ethylene. It has been found that a new a, ss-di- [benzimidazyl- (2)] -ethylene is obtained if a compound of the formula
EMI0001.0006
lets act on o-phenylenediamine at elevated temperature.
As compounds of the formula
EMI0001.0008
come maleic acid or its functional derivatives, e.g. B. Esters, into consideration.
If the dicarboxylic acid is used as the starting material, the reaction of the o-phenylenediamine with the compounds mentioned is advantageously carried out at 120-180, advantageously with the exclusion of oxygen. The new a, ss-di- [benzimidazyl- (2)] - ethylene forms an almost colorless powder that is insoluble or sparingly soluble in water and in the usual organic solvents. It is taken up by dilute hot hydrochloric acid to form a greenish yellow solution. It can be used as an intermediate, e.g.
B. for the manufacture of textile auxiliaries, also found as op table bleach application. The disodium salt of the new end product can also be used for the latter purpose. <I> Example: </I> 660 parts of o-phenylenediamine are heated with 116 parts of maleic acid from 120 to 160 within 3-5 hours with exclusion of air. As soon as the elimination of water subsides, the temperature is increased to around 190 and held at 190-195 for a short time until no more water escapes. It is allowed to cool and the excess o-phenylenediamine is removed by exhaustion with alcohol, benzene or another solvent.
The residue is dissolved in hot, dilute hydrochloric acid and the condensation product from the solution with an al kalischen means, z. B. with ammonia, precipitated, filtered off and washed neutral with water. It can be further purified via the hydrochloride.
The new product forms an almost colorless powder that is insoluble or sparingly soluble in water and the usual organic solvents. It is absorbed by dilute, hot hydrochloric acid to form a greenish-yellow solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240109T | 1942-12-23 | ||
| CH2488094X | 1942-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240109A true CH240109A (en) | 1945-11-30 |
Family
ID=25728476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240109D CH240109A (en) | 1942-12-23 | 1942-12-23 | Process for the preparation of a new a, B-di- (benzimidazyl- (2)) - ethylene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240109A (en) |
-
1942
- 1942-12-23 CH CH240109D patent/CH240109A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH240109A (en) | Process for the preparation of a new a, B-di- (benzimidazyl- (2)) - ethylene. | |
| AT163629B (en) | Process for the production of new imidazolines | |
| CH240111A (en) | Process for the preparation of a new a, B-di- (benzimidazyl- (2)) - ethylene. | |
| AT163820B (en) | Process for the preparation of a new condensation product of sulfanilamidoethylthiodiazole | |
| AT234681B (en) | Process for the preparation of new 1-methyl-1,2-di- [benzimidazolyl- (2 ')] - ethylene compounds | |
| CH259688A (en) | Process for the preparation of a biguanide derivative. | |
| CH259689A (en) | Process for the preparation of a biguanide derivative. | |
| CH268449A (en) | Process for the preparation of a basic ester. | |
| CH259684A (en) | Process for the preparation of a biguanide derivative. | |
| CH267592A (en) | Process for the preparation of a biguanide derivative. | |
| CH249041A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH267597A (en) | Process for the preparation of a biguanide derivative. | |
| CH269427A (en) | Process for the preparation of a biguanide derivative. | |
| CH259698A (en) | Process for the preparation of a biguanide derivative. | |
| CH240583A (en) | Process for the preparation of an N-substituted imino-di-fatty acid amide. | |
| CH316551A (en) | Process for the preparation of a diuretically active mercury compound | |
| CH259699A (en) | Process for the preparation of a biguanide derivative. | |
| CH259713A (en) | Process for the preparation of a biguanide derivative. | |
| CH267585A (en) | Process for the preparation of the new a- (benzimidazyl- (2)) - B- (N-ethyl-benzimidazyl- (2)) - ethylene. | |
| CH259693A (en) | Process for the preparation of a biguanide derivative. | |
| CH180688A (en) | Process for the preparation of 2,4-dinitro-3,6-dichloroaniline. | |
| CH254800A (en) | Process for the preparation of a biguanide derivative. | |
| CH259704A (en) | Process for the preparation of a biguanide derivative. | |
| CH269428A (en) | Process for the preparation of a biguanide derivative. | |
| CH261858A (en) | Process for the preparation of an anthraquinone dye. |