CH243780A - Process for the preparation of a new benzimidazole derivative. - Google Patents
Process for the preparation of a new benzimidazole derivative.Info
- Publication number
- CH243780A CH243780A CH243780DA CH243780A CH 243780 A CH243780 A CH 243780A CH 243780D A CH243780D A CH 243780DA CH 243780 A CH243780 A CH 243780A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfuric acid
- water
- benzimidazole derivative
- benzene
- preparation
- Prior art date
Links
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 238000009994 optical bleaching Methods 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NFPVUSMKBONLIX-UHFFFAOYSA-N O.O.O.[S] Chemical compound O.O.O.[S] NFPVUSMKBONLIX-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 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)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Paper (AREA)
Description
Verfahren zur Herstellung eines neuen Benzimidazolderivates. Es wurde gefunden, dass man zu einem neuen Benzimidazolderivat gelangt, wenn man ein Sulfonierungsmittel auf 1,4-Di- rbenzimidazyl-(2')]-benzol einwirken lässt.
Als Sulfonierungsmittel kann man zum Beispiel Schwefelsäuremonohydrat, Schwe- feltriogyd enthaltende Schwefelsäure, ferner Chlorsulfonsäure verwenden.
Die Sulfonierung wird zweckmässig in der Weise ausgeführt, dass man das 1,4-Di- [benzimidazyl-(2')]-benzol in Schwefelsäure monohydrat bei Raumtemperatur löst, Schwe- feltriogyd enthaltende Schwefelsäure zugibt und die Umsetzung bei 50 bis 100 , zweck mässig bei 70 , zu Ende führt.
Das Natriumsalz des neuen Erzeugnisses bildet ein helles, in Wasser lösliches Pulver. Seine verdünnte wässerige Lösung fluores ziert am Tageslicht oder im ultravioletten Licht violett. Es kann als optisches Bleich mittel Anwendung finden. <I>Beispiel:</I> 7,5 Teile 1,4-Di-[benzimidazyl-(2')]-ben- zol werden in 75 Teilen Schwefelsäuremono- hydrat bei 20 bis 30 gelöst und dann auf 70 erhitzt. Dazu werden 20 Teile rauchende Schwefelsäure, enthaltend 24% Schwefel triogyd, getropft.
Man rührt bei 70<B>'</B>, bis sich eine Probe in sodaalkalischem Wasser klar auflöst, lässt abkühlen, giesst auf Eiswasser,: filtriert die abgeschiedene Sulfonsäure ab und wäscht mit Wasser neutral. Der Filter rückstand wird mit Wasser verrührt, mit Natriumcarbonat neutral gestellt und die Lö sung zur Trockne eingedampft. Man erhält ein helles Pulver, das in Wasser löslich ist. Die verdünnte wässerige Lösung fluoresziert am Tageslicht oder im ultravioletten Licht violett.
Process for the preparation of a new benzimidazole derivative. It has been found that a new benzimidazole derivative is obtained if a sulfonating agent is allowed to act on 1,4-di-benzimidazyl- (2 ')] benzene.
Sulfonating agents that can be used are, for example, sulfuric acid monohydrate, sulfuric acid containing sulfur triogide, and also chlorosulfonic acid.
The sulfonation is expediently carried out in such a way that the 1,4-di- [benzimidazyl- (2 ')] -benzene is dissolved in sulfuric acid monohydrate at room temperature, sulfuric acid containing sulfur trihydrate is added and the reaction is carried out at 50 to 100% moderate at 70, ends.
The sodium salt of the new product forms a light-colored powder that is soluble in water. Its dilute aqueous solution fluoresces violet in daylight or in ultraviolet light. It can be used as an optical bleaching agent. <I> Example: </I> 7.5 parts of 1,4-di- [benzimidazyl- (2 ')] -benzene are dissolved in 75 parts of sulfuric acid monohydrate at 20 to 30 and then heated to 70. To this end, 20 parts of fuming sulfuric acid, containing 24% sulfur triogide, are added dropwise.
The mixture is stirred at 70 <B> '</B> until a sample dissolves clearly in soda-alkaline water, allowed to cool, poured onto ice water: the sulfonic acid which has separated out is filtered off and washed neutral with water. The filter residue is stirred with water, neutralized with sodium carbonate and the solution evaporated to dryness. A light-colored powder is obtained which is soluble in water. The diluted aqueous solution fluoresces violet in daylight or in ultraviolet light.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243780T | 1943-07-02 | ||
| CH235570T | 1943-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH243780A true CH243780A (en) | 1946-07-31 |
Family
ID=25728021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH243780D CH243780A (en) | 1943-07-02 | 1943-07-02 | Process for the preparation of a new benzimidazole derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH243780A (en) |
-
1943
- 1943-07-02 CH CH243780D patent/CH243780A/en unknown
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