CH244346A - Process for the preparation of a benzenesulfonamide derivative. - Google Patents
Process for the preparation of a benzenesulfonamide derivative.Info
- Publication number
- CH244346A CH244346A CH244346DA CH244346A CH 244346 A CH244346 A CH 244346A CH 244346D A CH244346D A CH 244346DA CH 244346 A CH244346 A CH 244346A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazine
- preparation
- benzenesulfonamido
- benzenesulfonamide derivative
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KAPFAVLCJMCLFV-UHFFFAOYSA-N n-pyrazin-2-ylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CN=CC=N1 KAPFAVLCJMCLFV-UHFFFAOYSA-N 0.000 description 3
- YEAICDDXRUOCKJ-UHFFFAOYSA-N 4-amino-n-pyrazin-2-ylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=CC=N1 YEAICDDXRUOCKJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 2
- SCWBAEJPJWWUBB-UHFFFAOYSA-N 4-nitro-n-pyrazin-2-ylbenzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CN=CC=N1 SCWBAEJPJWWUBB-UHFFFAOYSA-N 0.000 description 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- -1 benzenesulfonic acid halides Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D241/20—Nitrogen atoms
- C07D241/22—Benzenesulfonamido pyrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Benzolsulfonamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung des im Patent Nr.240222 beschriebenen Benzolsulfonamid- derivates, das dadurch gekennzeichnet ist, dass man ein Benzolsul'fonamido-pyrazin, das in p-Stellung einen durch Reduktion in die Aminogruppe überführbaren Substituenten aufweist, mit einem reduzierenden Mittel be handelt.
Die so erhaltene Verbindung soll als Heil mittel oder als Zwischenprodukt Verwendung finden.
Das, Benzolsulfonamido-pyrazin, das in p-Stellung zur Sulfonamidgruppe einen durch Reduktion in die Aminogruppe überführbaren Substituenten enthält, kann auf verschiedene Art und Weise gewonnen werden.
Besonders geeignet ist die Umsetzung der entsprechen den reaktionsfähigen Benzolsulfonsäurederi- vate, insbesondere der Benzolsulfonsäurehalo- genide, mit Pyrazin-Verbindungen, die eine Gruppe enthalten, die mit dem Benzolsulfon- säurederivat ein Benzolsulfonamido-pyrazin zu bilden vermag, insbesondere mit Amino- pyrazin. Man kann aber auch entsprechende Sulfonamide der Formel RSO@NHY,
in der Y einen bei der nachfolgenden Reaktion sich abspaltenden Rest bedeutet, mit Halogen- pyrazinen umsetzen, oder andere dem Fach mann geläufige Herstellungsmethoden be nutzen.
Beispiel <I>1:</I> 280g (p-Nitro-benzolsulfonamido)-pyra- zin, das durch Kondensation von p-Nitro- benzolsulfonchlorid mit Aminopyrazin erhal ten wurde, werden .in der 50fachen Menge absolutem Alkohol gelöst und mit 10 Ge wichtsprozent eines Nickel-Träger-Katalysa- tors. im Rührautoklaven mit Wasserstoff unter einem Überdruck von 50 Atm. bis zur Beendigung der Wasserstoffaufnahme bei 100-120 behandelt.
Nach dem Erkalten wird vom Katalysator abfiltriert und die alkoholische Lösung eingedampft. Dabei fällt das gebildete (p-Arnino-benzolsulfonamido)- pyrazin kristallin an. Die Verbindung kann zur Reinigung aus verdünntem Alkohol, ge gebenenfalls, unter Zusatz von Tierkohle, um kristallisiert werden. Schmelzpunkt 247 (unter Zersetzung).
Beispiel <I>2:</I> 280g (p-Nütro-benzolsulfonamido)-pyra- zin werden mittels Zinnchlorür und Salzsäure reduziert. Dass gebildete (p-Amino-benzolsul- fonamido)-pyrazin wird isoliert und gegebe nenfalls umkristallisiert. Schmelzpunkt 247 (unter Zersetzung).
Das entstandene p-Aminobenzolsulfon- amidderivat lässt sich auch in Form seiner Salze; z. B. des Natrituns oder des Kalziums, isolieren.
Process for the preparation of a benzenesulfonamide derivative. The subject of the present patent is a process for the preparation of the benzenesulfonamide derivative described in the patent No. 240222, which is characterized in that a benzenesulfonamido-pyrazine which has a substituent which can be converted into the amino group by reduction in the p-position is used a reducing agent.
The compound thus obtained is said to be used as a medicinal product or as an intermediate product.
The benzenesulfonamido-pyrazine, which contains a substituent which can be converted into the amino group by reduction in the p-position to the sulfonamide group, can be obtained in various ways.
The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with pyrazine compounds which contain a group which is able to form a benzenesulfonamido-pyrazine with the benzenesulfonic acid derivative, in particular with aminopyrazine, is particularly suitable. But you can also use corresponding sulfonamides of the formula RSO @ NHY,
in which Y denotes a radical which is split off in the subsequent reaction, react with halopyrazines, or use other production methods familiar to those skilled in the art.
Example <I> 1: </I> 280 g (p-nitro-benzenesulfonamido) -pyrazine, which was obtained by condensation of p-nitrobenzenesulfonic chloride with aminopyrazine, are dissolved in 50 times the amount of absolute alcohol and mixed with 10 Ge weight percent of a nickel-supported catalyst. in a stirred autoclave with hydrogen under a pressure of 50 atm. treated at 100-120 until hydrogen uptake ceases.
After cooling, the catalyst is filtered off and the alcoholic solution is evaporated. The (p-amino-benzenesulfonamido) pyrazine formed is obtained in crystalline form. For purification, the compound can be crystallized from dilute alcohol, if necessary with the addition of animal charcoal. Melting point 247 (with decomposition).
Example <I> 2: </I> 280 g (p-Nutro-benzenesulfonamido) -pyrazine are reduced by means of tin chloride and hydrochloric acid. The (p-amino-benzenesulfonamido) pyrazine formed is isolated and, if necessary, recrystallized. Melting point 247 (with decomposition).
The resulting p-aminobenzenesulfonamide derivative can also be used in the form of its salts; z. B. of sodium or calcium, isolate.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE244346X | 1939-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH244346A true CH244346A (en) | 1946-09-15 |
Family
ID=5925430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH244346D CH244346A (en) | 1939-05-23 | 1941-05-23 | Process for the preparation of a benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH244346A (en) |
-
1941
- 1941-05-23 CH CH244346D patent/CH244346A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2610225A1 (en) | NEW ALUMINUM SALT, THEIR PRODUCTION AND THE COMPOSITIONS THAT CONTAIN THEM | |
| CH244346A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH244348A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| DE1129504B (en) | Process for the preparation of a new, analeptically active alpha-aminopropiophenone and its acid addition salts | |
| CH244347A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH250000A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH244345A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH250003A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH403798A (en) | Process for the preparation of a medicament containing amprotropin | |
| CH249997A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH250002A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH250001A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH242490A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH250007A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH242492A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH242493A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| AT359479B (en) | METHOD FOR PRODUCING NEW BENZOE ACIDS AND THEIR ESTERS AND SALTS | |
| CH240222A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH239691A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH468979A (en) | Process for the preparation of benzenesulfonylureas | |
| CH239689A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH242487A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH250004A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH242491A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH239686A (en) | Process for the preparation of a new benzenesulfonamide derivative. |