CH201204A - Process for preparing a sulfonic acid amide compound. - Google Patents
Process for preparing a sulfonic acid amide compound.Info
- Publication number
- CH201204A CH201204A CH201204DA CH201204A CH 201204 A CH201204 A CH 201204A CH 201204D A CH201204D A CH 201204DA CH 201204 A CH201204 A CH 201204A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid amide
- acid
- sulfonic acid
- amide compound
- preparing
- 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 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- JWDLYKTZCRIGNW-UHFFFAOYSA-N 2-phenyl-n-(4-sulfamoylphenyl)acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)CC1=CC=CC=C1 JWDLYKTZCRIGNW-UHFFFAOYSA-N 0.000 claims description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 239000003279 phenylacetic acid Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010061372 Streptococcal infection Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method 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. Es wurde gefunden, dass die Acylamino- benzolsufonsäureamide, deren Acylrest min destens 5 Kohlenstoffatome enthält, thera peutisch, im besonderen gegen Streptokokken- infektionen gut wirksame Produkte darstellen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung einer Sul- fonsäureamidverbindung, welches dadurch ge kennzeichnet ist, dass man eine Verbindung, die sich von der Phenylessigsäure dadurch unterscheidet, dass sie an Stelle der OH- Gruppe einen reaktionsfähigeren Substituenten besitzt, auf 4-Aminobenzolsulfonsäureamid einwirken lässt. Als reaktionsfähige Abkömm linge der Phenylessigsäure kommen ihre Ha logenide, im besonderen ihr Chlorid, ferner ihre Ester und ihr Anhydrid in Betracht.
Bei Verwendung der Halogenide arbeitet man zweckmässig in Gegenwart eines säurebinden den Mittels, vorzugsweise Pyridin. Die Ab scheidung des Umsetzungsproduktes aus der Reaktionsmischung kann in an sich üblicher Weise, zum Beispiel durch Behandeln des Reaktionsproduktes mit Wasser oder ver dünnter Säure erfolgen. Nach Umkristalli- sieren des Rohproduktes, zum Beispiel aus Methanol erhält man das 4-Phenylacetyl- benzolsulftinsäureamid in farblosen Kristallen vom Schmelzpunkt<B>2060.</B> Es ist in Wasser und verdünnten Säuren unlöslich und soll therapeutische Anwendung finden.
<I>Beispiel:</I> 17,2 g 4-Aminobenzolsulfonsäureamid wer den in 50 cm' Pyridin gelöst und mit 16 g Phenylessigsäurechlorid versetzt. Nach halb stündigem Erhitzen auf dem Wasserbad wird in verdünnte kalte Salzsäure gegossen, der Niederschlag abgesaugt, mit Salzsäure und Wasser gewaschen und aus Methanol um kristallisiert. Man erhält das 4-Phenylacetyl- amino-benzolsulfonsäureamid in farblosen Kri stallen vom Schmelzpunkt<B>2060,</B>
Process for preparing a sulfonic acid amide compound. It has been found that the acylamino-benzenesulfonic acid amides, the acyl radical of which contains at least 5 carbon atoms, are therapeutically effective products, in particular against streptococcal infections.
The subject of the present patent is a process for the preparation of a sulphonic acid amide compound, which is characterized in that a compound which differs from phenylacetic acid in that it has a more reactive substituent instead of the OH group is placed on 4-aminobenzenesulphonic acid amide can act. Its halides, in particular its chloride, and also its esters and anhydride come into consideration as reactive derivatives of phenylacetic acid.
When using the halides, it is expedient to work in the presence of an acid-binding agent, preferably pyridine. The separation of the reaction product from the reaction mixture can be carried out in a conventional manner, for example by treating the reaction product with water or dilute acid. After recrystallization of the crude product, for example from methanol, the 4-phenylacetylbenzenesulftinamide is obtained in colorless crystals with a melting point of 2060. It is insoluble in water and dilute acids and is said to be of therapeutic use.
<I> Example: </I> 17.2 g of 4-aminobenzenesulfonic acid amide are dissolved in 50 cm of pyridine and mixed with 16 g of phenylacetic acid chloride. After half an hour of heating on the water bath, it is poured into dilute cold hydrochloric acid, the precipitate is filtered off with suction, washed with hydrochloric acid and water and recrystallized from methanol. The 4-phenylacetylamino-benzenesulfonic acid amide is obtained in colorless crystals with a melting point of <B> 2060 </B>
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201204X | 1936-04-18 | ||
| CH197427T | 1937-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201204A true CH201204A (en) | 1938-11-15 |
Family
ID=25722983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201204D CH201204A (en) | 1936-04-18 | 1937-04-03 | Process for preparing a sulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201204A (en) |
-
1937
- 1937-04-03 CH CH201204D patent/CH201204A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH201204A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH201206A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH201205A (en) | Process for preparing a sulfonic acid amide compound. | |
| DE662066C (en) | Process for the preparation of substituted amides of fatty aromatic monocarboxylic acids | |
| CH201203A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH312531A (en) | Process for making a pyridazone. | |
| CH201207A (en) | Process for preparing a sulfonic acid amide compound. | |
| AT146967B (en) | Process for the production of heavy metal compounds of the porphine series. | |
| AT166702B (en) | Process for the preparation of new halogenated pyrimidyl mercaptocarboxylic acids and their derivatives | |
| AT33110B (en) | Process for the preparation of alkyloxyacetyl compounds of alcohols of the hydroaromatic series. | |
| DE931947C (en) | Process for the preparation of 20, 21-pregnanketol esters | |
| AT164549B (en) | Process for the production of sterol degradation products | |
| AT142027B (en) | Process for the preparation of acyl derivatives of the dihydrofollicle hormone. | |
| AT42151B (en) | Process for the preparation of mild laxatives from phenolphthalein. | |
| CH227069A (en) | Process for the preparation of a cyclopentano-dimethyl-polyhydrophenanthrene-carboxylic acid. | |
| CH206120A (en) | Process for the preparation of a new ester. | |
| CH249042A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH211649A (en) | Process for the preparation of a new enol derivative containing the sterol core. | |
| CH350285A (en) | Process for the production of new fabrics of the Pregnan series | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| DE2010221A1 (en) | ||
| CH316733A (en) | Process for the production of 2,5-dichloroterephthalic acid | |
| CH260304A (en) | Process for the preparation of B-benzyl mercapto valine. | |
| CH90806A (en) | Process for the preparation of a dioxynaphtoylbenzoic acid ester. | |
| CH213181A (en) | Process for the preparation of a monoester of the androstene series. |