CH185343A - Process for the preparation of a sulfenamide. - Google Patents
Process for the preparation of a sulfenamide.Info
- Publication number
- CH185343A CH185343A CH185343DA CH185343A CH 185343 A CH185343 A CH 185343A CH 185343D A CH185343D A CH 185343DA CH 185343 A CH185343 A CH 185343A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- sulfenamide
- hexahydroethylaniline
- benzene
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung eines Sulfonamids. Gegenstand vorliegender Erfindung ist die Herstellung eines Sulfonamids durch Pehandlung von 2-Merkaptobenzothiazol und Hexahydroäthylanilin mit Natriumhypo- chlorit. Die Umsetzung wird in wässrigem 1ledium mit oder ohne Zusatz indifferenter organischer Lösungsmittel durchgeführt.
Sie geht schon bei niedriger Temperatur vor sich, kann aber durch Erwärmen beschleunigt werden.
Das nach diesem Verfahren erhältliche bereits bekannte Sulfonamid kann als Hilfs stoff in der Kautschukindustrie Verwendung finden.
Beispiel: 50 kg 2-;VIercaptobenzothiazol, mit<B>300</B> Liter Wasser verrührt, werden mit 114 kg Hexahydroäthylanilin versetzt und durch Er wärmen auf 50 in Lösung gebracht. Nach Rückkühlen auf 35 läuft eine wässrige Lö sung von 21,6 kg Natriumhypochlorit inner halb 6 Stunden zu.
Nach einstündigem Nachrühren wird mit etwa 300 Liter Wasser verdünnt. Die wässrige Lösung wird von den öligen Anteilen abgetrennt. Letztere werden in Benzol aufgenommen, worauf die ben- zolische Lösung zwecks Befreiung vom Übei- schiissio; angewandten Hexahydroäthylanilin mit sehr verdünnter Salzsäure kalt verrührt und dann neutral gewaschen wird.
Nach Abdestillieren des Benzols unter verminder tem Druck hinterbleibt das Benzothiazolyl- 2-sulfenhexahydroäthylanilid:
EMI0001.0038
als dickes 01 in einer Menge von 67 kg, entsprechend 75,5% der Theorie.
Process for the preparation of a sulfonamide. The present invention relates to the preparation of a sulfonamide by treating 2-mercaptobenzothiazole and hexahydroethylaniline with sodium hypochlorite. The reaction is carried out in aqueous 1ledium with or without the addition of inert organic solvents.
It already takes place at a low temperature, but it can be accelerated by heating.
The already known sulfonamide obtainable by this process can be used as an auxiliary material in the rubber industry.
Example: 50 kg of 2-; VIercaptobenzothiazole, stirred with <B> 300 </B> liters of water, are mixed with 114 kg of hexahydroethylaniline and brought into solution by heating to 50. After cooling back to 35, an aqueous solution of 21.6 kg of sodium hypochlorite runs in within 6 hours.
After stirring for one hour, the mixture is diluted with about 300 liters of water. The aqueous solution is separated from the oily components. The latter are taken up in benzene, whereupon the benzene solution for the purpose of liberation from the ubichiissio; applied hexahydroethylaniline is stirred cold with very dilute hydrochloric acid and then washed neutral.
After the benzene has been distilled off under reduced pressure, the benzothiazolyl-2-sulfenhexahydroethylanilide remains:
EMI0001.0038
as thick 01 in an amount of 67 kg, corresponding to 75.5% of theory.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH182394T | 1935-02-14 | ||
CH185343T | 1935-02-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH185343A true CH185343A (en) | 1936-07-15 |
Family
ID=25720701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH185343D CH185343A (en) | 1935-02-14 | 1935-02-14 | Process for the preparation of a sulfenamide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH185343A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2762814A (en) * | 1953-11-27 | 1956-09-11 | Monsanto Chemicals | Production of vulcanization accelerators |
-
1935
- 1935-02-14 CH CH185343D patent/CH185343A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2762814A (en) * | 1953-11-27 | 1956-09-11 | Monsanto Chemicals | Production of vulcanization accelerators |
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