CH208087A - Process for preparing a sulfonic acid amide compound. - Google Patents
Process for preparing a sulfonic acid amide compound.Info
- Publication number
- CH208087A CH208087A CH208087DA CH208087A CH 208087 A CH208087 A CH 208087A CH 208087D A CH208087D A CH 208087DA CH 208087 A CH208087 A CH 208087A
- Authority
- CH
- Switzerland
- Prior art keywords
- amide compound
- sulfonic acid
- acid amide
- preparing
- sodium
- Prior art date
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- CSOHXJHVFCKHQB-UHFFFAOYSA-N 4-[(4-nitrophenyl)sulfonylamino]benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 CSOHXJHVFCKHQB-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JYPXJELCOVLQJZ-UHFFFAOYSA-N 4-[(4-aminophenyl)sulfonylamino]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=C(S(O)(=O)=O)C=C1 JYPXJELCOVLQJZ-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- KSVSZLXDULFGDQ-UHFFFAOYSA-M sodium;4-aminobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1 KSVSZLXDULFGDQ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer Sulfonsäureamidverbindung. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung einer Sulfon- säureamidverbindung, welches dadurch ge kennzeichnet ist, dass man ein Alkalisalz der 4-(p-Nitrobenzolsulfonamido) -benzolsulfon- säure reduziert und das erhaltene Produkt als Natriumsalz der 4-(p-Aminobenzolsulfon- amido)-benzolsulfonsäure abscheidet. Das so erhältliche Natriumsalz ist in Wasser löslich.
Es soll therapeutische Anwendung finden. <I>Beispiel:</I> 30 g Natriumsalz der 4-(p-Nitrobenzol- sulfonamido) - benzolsulfonsäure werden zu einer kochenden Mischung von 50 g Eisen spänen, 200 cm' Wasser und 2 cm' Essig säure gegeben und eine Stunde unter Rüh ren zum Sieden erhitzt.
Nach Abkühlen wird mit Natronlauge alkalisch gemacht, fil triert und aus dem Filtrat gegebenenfalls nach vorherigem Einengen und Neutrali- sieren das Natriumsalz der 4-(p-Aminoben- zolsulfonamido)-benzolsuHonsäure durch Zu satz von Natriumchlorid ausgesalzen oder durch Zusatz von Alkohol ausgefällt.
Zur Herstellung des Ausgangsstoffes wird eine Lösung von 20 g 4-aminobenzol- sulfonsaurem Natrium und 25g Natrium- aeetat in 200 cm@ Wasser bei etwa 40 mit 24 g 4-Nitrobenzolsulfonsäurechlorid gerührt, bis eine Probe des Reaktionsgemisches, mit Salzsäure versetzt, kein Natriumnitrit mehr aufnimmt. Auf Zusatz von Natriumchlorid fällt das Natriumsalz der 4-(p-Nitrobenzol- sulfonamido)
-benzolsulfonsäure, das durch Umlösen aus wenig Wasser in hellgelben Kri stallen anfällt.
Process for preparing a sulfonic acid amide compound. The subject of the present patent is a process for the preparation of a sulfonic acid amide compound, which is characterized in that an alkali salt of 4- (p-nitrobenzenesulfonamido) -benzenesulfonic acid is reduced and the product obtained is reduced as the sodium salt of 4- (p-aminobenzenesulfone - Amido) -benzenesulfonic acid is deposited. The sodium salt thus obtainable is soluble in water.
It should find therapeutic application. <I> Example: </I> 30 g of the sodium salt of 4- (p-nitrobenzenesulfonamido) - benzenesulfonic acid are added to a boiling mixture of 50 g of iron shavings, 200 cm 'of water and 2 cm' of acetic acid and taken for one hour Stir heated to boiling.
After cooling, it is made alkaline with sodium hydroxide solution, filtered and the sodium salt of 4- (p-aminobenzenesulfonamido) -benzenesulfonic acid is salted out from the filtrate by adding sodium chloride or precipitated by adding alcohol, if necessary after prior concentration and neutralization.
To prepare the starting material, a solution of 20 g of sodium 4-aminobenzenesulfonate and 25g of sodium acetate in 200 cm @ water at about 40 is stirred with 24 g of 4-nitrobenzenesulfonyl chloride until a sample of the reaction mixture has been mixed with hydrochloric acid and no more sodium nitrite records. When sodium chloride is added, the sodium salt of 4- (p-nitrobenzenesulfonamido)
-benzenesulfonic acid, which is obtained by dissolving a little water in light yellow crystals.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE208087X | 1936-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH208087A true CH208087A (en) | 1939-12-31 |
Family
ID=5794041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH208087D CH208087A (en) | 1936-08-20 | 1937-07-27 | Process for preparing a sulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH208087A (en) |
-
1937
- 1937-07-27 CH CH208087D patent/CH208087A/en unknown
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