CH206624A - Process for preparing a sulfonic acid amide compound. - Google Patents
Process for preparing a sulfonic acid amide compound.Info
- Publication number
- CH206624A CH206624A CH206624DA CH206624A CH 206624 A CH206624 A CH 206624A CH 206624D A CH206624D A CH 206624DA CH 206624 A CH206624 A CH 206624A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- amide compound
- sulfonic acid
- acid amide
- salt
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- KGQGBLKODLWURR-UHFFFAOYSA-N 3-[(4-aminophenyl)sulfonylamino]benzoic acid Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC(C(O)=O)=C1 KGQGBLKODLWURR-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- -1 sulfonic acid halide Chemical class 0.000 description 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 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
- 238000005187 foaming Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
-
- 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 Patentes ist ein Verfah ren zur Darstellung einer SulfonsäuTeamid- verbindung, welches dadurch gekennzeichnet ist, dass man ein p-Acylaminobenzolsulfon- säurehalogenid mit einem 3-aminobenzoe- sauren Salz zur Umsetzung bringt, das Um setzungsprodukt verseift und das Verseifungs- produkt in Form des Natriumsalzes abschei det.
Die Umsetzung zwischen dem 3-amino- henzolsauren Salz und dem p-Acylamino- benzolsulfonsäurehalogenid erfolgt zweck mässig in Gegenwart eines säurebindenden Mittels, z. B. Natriumcarbonat. Als p-Acyl- aminobenzolsulfonsäur.ehalogenid wird vor zugsweise p - AcetylaminobenzoIsulfons.äure- chlorid verwendet.
Zur Venseifung eignet sich z. B. Natron lauge.
Das so erhältliche Natriumsalz der 3-(p- Aminobenzolsulfonamido)-benzoesäure ist in Wasser löslich. Es soll therapeutische An wendung finden. Beispiel: Zu einer Lösung von 27,4 g 3-Amino- benzoesäure, 8 g Natriumhydrogyd und 30 g Natriumcarbonat in 200 ein' Wasser fügt man 48 g p-Acetylaminobenzolsulfonsäure- chlorid und rührt bei 3,0-40',
bis alles klar gelöst ist und eine Probe auf Zusatz von Salzsäure keine salpetrige Säure mehr auf nimmt. Man entfärbt mit Kohle, filtriert und fällt mit Salzsäure die 3-(p-Acetyl- a,minobenzolsulfonamido)-ben.zoesäure. Durch Umlösen aus Alkohol erhält man sie in farb losen Kristallen, die bei<B>261'</B> unter Schäu men schmelzen.
Die Aoetylverbindung wird mit der fünf fachen Menge 20%iger Natronlauge unter Rückfluss zwei Stunden zum Sieden erhitzt. Nach Abkühlen wird filtriert und aus dem Filtrat durch Ansäuern die 3-(p-Aminoben- zolsulfonamida) - benzoesäure abgeschieden. Diese wird in der berechneten Menge Natron lauge oder Natriumcarbonat gelöst und als Natriumsalz durch Zusatz von Natriumchlo- rid oder Alkohol abgeschieden.
Process for preparing a sulfonic acid amide compound. The subject of the patent is a process for the preparation of a sulfonic acid amide compound, which is characterized in that a p-acylaminobenzenesulfonic acid halide is reacted with a 3-aminobenzoic acid salt, the reaction product is saponified and the saponification product is shaped of the sodium salt separates.
The reaction between the 3-amino-benzene acid salt and the p-acylamino-benzenesulfonic acid halide is expediently carried out in the presence of an acid-binding agent, e.g. B. sodium carbonate. The p-acylaminobenzene sulfonic acid halide used is preferably p-acetylaminobenzene sulfonic acid chloride.
For Venseifung z. B. caustic soda.
The sodium salt of 3- (p-aminobenzenesulfonamido) benzoic acid thus obtainable is soluble in water. It should find therapeutic use. Example: 48 g of p-acetylaminobenzenesulfonic acid chloride are added to a solution of 27.4 g of 3-aminobenzoic acid, 8 g of sodium hydrogen and 30 g of sodium carbonate in 200 'water and the mixture is stirred at 3.0-40',
until everything is clearly dissolved and a sample for the addition of hydrochloric acid no longer absorbs nitrous acid. It is decolorized with charcoal, filtered and 3- (p-acetyl-a, minobenzenesulfonamido) -benzoic acid is precipitated with hydrochloric acid. Dissolving them from alcohol gives them colorless crystals which, at <B> 261 '</B>, melt under foaming.
The acetyl compound is heated to boiling under reflux for two hours with five times the amount of 20% strength sodium hydroxide solution. After cooling, it is filtered and the 3- (p-aminobenzenesulfonamida) benzoic acid is separated out from the filtrate by acidification. This is dissolved in the calculated amount of caustic soda or sodium carbonate and deposited as a sodium salt by adding sodium chloride or alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE206624X | 1936-08-20 | ||
| CH202106T | 1937-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206624A true CH206624A (en) | 1939-08-15 |
Family
ID=25723767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206624D CH206624A (en) | 1936-08-20 | 1937-07-27 | Process for preparing a sulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206624A (en) |
-
1937
- 1937-07-27 CH CH206624D patent/CH206624A/en unknown
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