CH204158A - Process for preparing an aminobenzenesulfonic acid amide compound. - Google Patents
Process for preparing an aminobenzenesulfonic acid amide compound.Info
- Publication number
- CH204158A CH204158A CH204158DA CH204158A CH 204158 A CH204158 A CH 204158A CH 204158D A CH204158D A CH 204158DA CH 204158 A CH204158 A CH 204158A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid amide
- acid
- preparing
- aminobenzenesulfonic acid
- amide compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 aminobenzenesulfonic acid amide compound Chemical class 0.000 title description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- OHVAGCOJNICDKZ-UHFFFAOYSA-N 2-phenoxy-n-(4-sulfamoylphenyl)acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)COC1=CC=CC=C1 OHVAGCOJNICDKZ-UHFFFAOYSA-N 0.000 description 2
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction 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 Aminobenzolsulfonsäureamidverbindung. Gemäss Angaben des Hauptpatentes sind gewisse Aminoacyl- und Oxyacylaminobenzol- sulfonsäureamide, sowie deren Substitutions- produkte durch ihre Wirkung gegen bakterielle Infektionskrankheiten ausgezeichnet.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von Phenoxy- acetylaminobenzol-4-sulfonsäureamid, welches dadurch gekennzeichnet ist, dass man auf 4- Aminobenzolsulforisäureamid ein für Acylie- rungszwecke geeignetes Derivat der Phenoxy- essigsäure einwirken lässt. Als Derivate der Phenoxyessigsäure kommen in erster Linie das Phenoxyessigsäurearibydrid und das Phen- oxyessigsäurechlorid in Betracht.
Bei Ver wendung des Chlorids wird zweckmässig ein salzsäurebindendes Mittel, z. B. Natrium- acetat, der Reaktionsmischung zugesetzt. Die Umsetzung erfolgt zweckmässig in Gegenwart von Wasser und unter Erwärmen. Das so erhältliche Phenoxyacetylaminobenzol-4-sul- fonsäureamid bildet farblose Kristalle vom Schmelzpunkt 205 0. Es soll therapeutische Anwendung finden. <I>Beispiel:</I> 20,8g Hydrochlorid des 4-Aminobenzol- sulfonsäureamids werden in 200 eins. Wasser gelöst und 17 g Phenoxyessigsäurechlorid zu gegeben.
Die Mischung wird unter Rühren auf dem Wasserbad erwärmt und die kongo saure Reaktion durch allmähliche Zugabe von festem Natriumacetat abgestumpft. Das aus fallende Phenoxyacetylarninobenzol-4-sulfon- säureamid wird abgesaugt. Zur Reinigung von etwas beigemengter Phenoxyessigsäure wird es mit kalter 5 %iger Natriumcarbonat- lösung ausgezogen. Es schmilzt bei 205 0.
Process for preparing an aminobenzenesulfonic acid amide compound. According to the main patent, certain aminoacyl- and oxyacylaminobenzenesulfonic acid amides, as well as their substitution products, are distinguished by their effectiveness against bacterial infectious diseases.
The subject of the present patent is a process for the preparation of phenoxyacetylaminobenzene-4-sulfonic acid amide, which is characterized in that a derivative of phenoxyacetic acid suitable for acylation purposes is allowed to act on 4-aminobenzenesulfonic acid amide. Phenoxyacetic acid aribydride and phenoxyacetic acid chloride are primarily suitable as derivatives of phenoxyacetic acid.
When using the chloride, a hydrochloric acid binding agent such. B. sodium acetate, added to the reaction mixture. The reaction is expediently carried out in the presence of water and with heating. The phenoxyacetylaminobenzene-4-sulphonic acid amide which can be obtained in this way forms colorless crystals with a melting point of 205 0. It is said to be of therapeutic use. <I> Example: </I> 20.8 g of hydrochloride of 4-aminobenzenesulfonic acid amide become one in 200. Dissolved water and added 17 g of phenoxyacetic acid chloride.
The mixture is heated on the water bath while stirring and the Congo acidic reaction is blunted by the gradual addition of solid sodium acetate. The phenoxyacetylarninobenzene-4-sulfonic acid amide which precipitates is filtered off with suction. To clean some of the added phenoxyacetic acid, it is extracted with cold 5% sodium carbonate solution. It melts at 205 0.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE204158X | 1936-02-06 | ||
| CH199315T | 1937-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204158A true CH204158A (en) | 1939-04-15 |
Family
ID=25723250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204158D CH204158A (en) | 1936-02-06 | 1937-01-12 | Process for preparing an aminobenzenesulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204158A (en) |
-
1937
- 1937-01-12 CH CH204158D patent/CH204158A/en unknown
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