CH210754A - Process for preparing a sulfonic acid amide compound. - Google Patents
Process for preparing a sulfonic acid amide compound.Info
- Publication number
- CH210754A CH210754A CH210754DA CH210754A CH 210754 A CH210754 A CH 210754A CH 210754D A CH210754D A CH 210754DA CH 210754 A CH210754 A CH 210754A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- acid amide
- amide compound
- so2r
- preparing
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 4
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 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 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- NHQZAKDAFJVQSN-UHFFFAOYSA-N 4-[(2-phenylacetyl)amino]benzenesulfonic acid Chemical compound C1(=CC=CC=C1)CC(=O)NC1=CC=C(C=C1)S(=O)(=O)O NHQZAKDAFJVQSN-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010061372 Streptococcal infection Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KYPIASPTMDEDQB-UHFFFAOYSA-N n,2-diphenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1=CC=CC=C1 KYPIASPTMDEDQB-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
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 Aeylamino- benzolsulfonsäureamide, 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 Herstellung einer Sul- fonsäureamidverbindung, dadurch gekenn zeichnet, dass man ein Phenylacetylamino- benzol, das in p-Stellung zur Aminogruppe den Substituenten -S02R enthält, wobei R einen reaktionsfähigen, bei der Reaktion sieh abspaltenden Rest bedeutet, durch Einwirken von Ammoniak in das 4-Phenylacety lamino- benzolsulfonsäureamid überführt.
Als Substi- tuenten der Formel -S02R eignen sich die Sulfonsäurehalogenidgruppen, im besonderen die Sulfochloridgruppe. Auch Sulfonsäure- estergruppen können Verwendung finden. Die Umsetzung erfolgt zweckmässig in alko holischer Lösung, nötigenfalls unter Erwärmen. Das so erhältliche, bisher noch nicht be kannte, 4 - Phenylacetylamino - benzolsulfon- säureamid bildet Kristalle vom Schmelzpunkt <B>2060.</B> Es soll therapeutische Anwendung finden.
<I>Beispiel:</I> 10 g 4-Phenylacetylamino-benzolsulfon- säure (dargestellt durch Einwirken von Phe- nylessigsäurechlorid auf 4-Aminobenzolsulfon- säure) werden mit 7 g Phosphorpentachlorid und 5 cm' Benzol im Wasserbad erwärmt, bis die Salzsäureentwicklung beendet ist.
Man nimmt das gebildete 4-Phenylamino- benzolsulfochlorid mit Chloroform und Eis auf, trennt das Chloroform ab, trocknet mit Natriumsulfat und versetzt mit methylalko- holischem Ammoniak. Nach Verdampfen des Lösemittels - wird der Rückstand mit 5%iger Salzsäure ausgezogen und der unge- löste Teil aus Methylalkohol umkristallisiert.
Das so erhaltene 4-Phenylacetylamino-ben- zol-sulfonsäureamid schmilzt bei<B>2060.</B>
Process for preparing a sulfonic acid amide compound. It has been found that the aylamino-benzenesulphonic acid amides, the acyl radical of which contains at least 5 carbon atoms, are therapeutically effective products, in particular against streptococcal infections.
The present patent relates to a process for the preparation of a sulphonic acid amide compound, characterized in that a phenylacetylamino-benzene which contains the substituent -SO2R in the p-position to the amino group, R being a reactive radical which is split off during the reaction , converted by the action of ammonia in the 4-phenylacety lamino-benzenesulfonic acid amide.
The sulfonic acid halide groups, in particular the sulfochloride group, are suitable as substituents of the formula -SO2R. Sulfonic acid ester groups can also be used. The reaction is expediently carried out in an alcoholic solution, if necessary with heating. The previously unknown 4-phenylacetylamino-benzenesulfonic acid amide obtainable in this way forms crystals with a melting point of <B> 2060. </B> It is intended to be used therapeutically.
<I> Example: </I> 10 g of 4-phenylacetylaminobenzenesulphonic acid (produced by the action of phenylacetic acid chloride on 4-aminobenzenesulphonic acid) are heated with 7 g of phosphorus pentachloride and 5 cm 'of benzene in a water bath until the development of hydrochloric acid is finished.
The 4-phenylaminobenzenesulfochloride formed is taken up with chloroform and ice, the chloroform is separated off, dried with sodium sulfate and mixed with methyl alcoholic ammonia. After evaporation of the solvent - the residue is extracted with 5% hydrochloric acid and the undissolved part is recrystallized from methyl alcohol.
The 4-phenylacetylamino-benzene-sulfonic acid amide thus obtained melts at <B> 2060. </B>
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE210754X | 1936-04-18 | ||
| CH202370T | 1937-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210754A true CH210754A (en) | 1940-07-31 |
Family
ID=25723797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210754D CH210754A (en) | 1936-04-18 | 1937-04-03 | Process for preparing a sulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210754A (en) |
-
1937
- 1937-04-03 CH CH210754D patent/CH210754A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1019290B (en) | Process for the production of new textile auxiliaries | |
| CH210753A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH210755A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH210756A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH210752A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH202370A (en) | Process for preparing a sulfonic acid amide compound. | |
| DE650999C (en) | Process for the production of ornithine and its derivatives | |
| DE587428C (en) | Process for the preparation of 1, 5, 5- and 1, 3, 5, 5-substituted barbituric acids | |
| DE539806C (en) | Process for the preparation of isopropylallylbarbituric acid | |
| AT69808B (en) | Process for the preparation of carbazole monosulfonic acids. | |
| AT296316B (en) | Process for the preparation of new benzodiazepine derivatives and their N-4-oxides | |
| AT146504B (en) | Process for the preparation of amides of pyrazine monocarboxylic acid. | |
| AT23907B (en) | Process for the preparation of orange disazo dyes for wool. | |
| CH180688A (en) | Process for the preparation of 2,4-dinitro-3,6-dichloroaniline. | |
| CH199679A (en) | Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-chloro-tetrahydropyridine. | |
| CH206629A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| CH220960A (en) | Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine. | |
| CH155773A (en) | Process for the production of a new condensation product. | |
| CH91106A (en) | Process for the preparation of a dioxynaphtoylbenzoic acid ester. | |
| CH231022A (en) | Process for the preparation of a new sulfanilic acid amide derivative. | |
| CH163888A (en) | Process for preparing an acylaminosulfonic acid chloride of the benzene series. | |
| CH207672A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH218521A (en) | Process for the preparation of a diphenyl sulfone derivative. | |
| CH201205A (en) | Process for preparing a sulfonic acid amide compound. |