CH217149A - Process for preparing a cyclic sulfonic acid amide compound. - Google Patents
Process for preparing a cyclic sulfonic acid amide compound.Info
- Publication number
- CH217149A CH217149A CH217149DA CH217149A CH 217149 A CH217149 A CH 217149A CH 217149D A CH217149D A CH 217149DA CH 217149 A CH217149 A CH 217149A
- Authority
- CH
- Switzerland
- Prior art keywords
- amide compound
- sulfonic acid
- acid amide
- cyclic sulfonic
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title claims description 4
- 125000004122 cyclic group Chemical group 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- -1 4-acetylaminobenzenesulfonic acid halide Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung einer cyclischen Salfonsäureamidrerbindung. Wie im Hauptpatent angegeben ist, ge langt man zu gegen Infektionskrankheiten hoch wirksamen Verbindungen, wenn man Abkömmlinge cyclischer Diamine herstellt, die in den beiden ringständigen Aminogrup- pen Benzolsulfonylreste tragen, deren p-Stel- lung mit dem Stickstoffatom einer stickstoff haltigen Gruppe verknüpft ist.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer cycli- schen Sulfonsäureamidverbindung, welches dadurch gekennzeichnet ist, dass man 4. 4'- Diaminodiphenyläther mit einem 4-Acetyl- aminobenzolsulfonsäurehalogenid umsetzt.
Die Umsetzung erfolgt zweckmässig in Gegen wart eines säurebindenden Mittels, vorzugs weise Pyridin. Die Abscheidung des Reak tionsproduktes erfolgt vorteilhaft unter Ein giessen der Reaktionsmischung in verdünnte 11Zineralsäure.
Der so erhältliche 4.4'-Bis-(4"-acetyl- aminobenzolsulfonamido) - diphenyläther bil- det ein weisses Kristallpulver, das nach voll ständiger Entwässerung bei<B>150'</B> schmilzt. Das neue Produkt soll therapeutische Anwen dung finden.
Beispiel: 20 g 4. 4'-Diaminodiphenyläther werden in 100 cm' Pyridin gelöst. Die Lösung wird allmählich mit 47 g 4-Acetylaminobenzosul- fonsäurechlorid versetzt und anschliessend eine Stunde auf dem siedenden RTasserbad erwärmt. Durch Einrühren der Reaktions- mischung in 300 am' konzentrierte Salzsäure, 300 cm' Wasser und Eis wird das Reaktions produkt abgeschieden, abgesaugt und mit Salzsäure und später mit Wasser ausge waschen.
Man reinigt den so erhaltenen 4 . 4'-Bis-(4"-acetylaminobenzol-sulfonamido)- diphenyläther durch Lösen in Natronlauge und Wiederausfällen mit Salzsäure. Die Ver bindung wird als weisses Kristallpulver erhal ten, das nach vollständiger Entwässerung bei <B>150,</B> schmilzt.
Process for the preparation of a cyclic sulfonic acid amide compound. As stated in the main patent, compounds that are highly effective against infectious diseases are obtained if derivatives of cyclic diamines are prepared which have benzenesulfonyl radicals in the two ring-attached amino groups whose p-position is linked to the nitrogen atom of a nitrogen-containing group.
The present patent relates to a process for the production of a cyclic sulfonic acid amide compound, which is characterized in that 4,4'-diaminodiphenyl ether is reacted with a 4-acetyl aminobenzenesulfonic acid halide.
The reaction is expediently carried out in the presence of an acid-binding agent, preferably pyridine. The reaction product is advantageously separated out by pouring the reaction mixture into dilute cineral acid.
The 4.4'-bis- (4 "-acetyl-aminobenzene-sulfonamido) -diphenyl ether which can be obtained in this way forms a white crystal powder which, after complete dehydration, melts at <B> 150 '</B>. The new product is intended to find therapeutic applications .
Example: 20 g of 4'-diaminodiphenyl ether are dissolved in 100 cm 'of pyridine. The solution is gradually mixed with 47 g of 4-acetylaminobenzosulphonic acid chloride and then heated for one hour on the boiling water bath. The reaction product is separated out by stirring the reaction mixture into 300 μm concentrated hydrochloric acid, 300 cm water and ice, filtered off with suction and washed out with hydrochloric acid and later with water.
The 4 obtained in this way is cleaned. 4'-Bis- (4 "-acetylaminobenzene-sulfonamido) - diphenyl ether by dissolving in sodium hydroxide solution and reprecipitation with hydrochloric acid. The compound is obtained as a white crystal powder which melts at <B> 150 </B> after complete dehydration.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE217149X | 1937-08-04 | ||
| CH208085T | 1938-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217149A true CH217149A (en) | 1941-09-30 |
Family
ID=25724494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217149D CH217149A (en) | 1937-08-04 | 1938-07-14 | Process for preparing a cyclic sulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217149A (en) |
-
1938
- 1938-07-14 CH CH217149D patent/CH217149A/en unknown
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