CH207675A - Process for preparing an aminobenzenesulfonic acid amide compound. - Google Patents
Process for preparing an aminobenzenesulfonic acid amide compound.Info
- Publication number
- CH207675A CH207675A CH207675DA CH207675A CH 207675 A CH207675 A CH 207675A CH 207675D A CH207675D A CH 207675DA CH 207675 A CH207675 A CH 207675A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminobenzenesulfonamido
- acid amide
- amide compound
- preparing
- aminobenzenesulfonic acid
- 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 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000007787 solid Substances 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 der im Patent 199315 beschriebe nen Erfindung sind gewisse Aminoacyl- und Ogyacyl-aminobenzolsulfonsäureamide sowie deren Substitutionsprodukte durch ihre Wir kung gegen bakterielle Infektionskrankheiten ausgezeichnet.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer Amino- benzolsulfonsäureamidverbindung, welches dadurch gekennzeichnet ist, dass man 4-(4'- Azobenzolsulfonamido) - benzolsulfondime - thylamid zu 4-(4'-AminobenzolsuHonamido)- benzolsulfondimethylamid reduziert. Die Re duktion erfolgt zweckmässig mittels Natrium- hydrosulfit in wässrig-alkalischer Lösung.
Aus der alkalischen Reaktionsmischung kann man das Reduktionsprodukt durch Ansäuern mit Essigsäure abscheiden. Bei der Reduktion ent steht zunächst das 4-4'-Hydrazobenzolsulfon- amido)-benzolsulfondimethylamid als Zwi schenstufe, das in der Regel ohne weiteres zum Endprodukt weiter reduziert wird. Bei Anwendung milderer Reduktionsmittel kann man die genannte Hydrazoverbindung in der Reaktionsmischung feststellen; sie wird dann durch stärker wirkende Reduktionsmittel in das Endprodukt übergeführt.
Das so erhältliche 4-(4'-Aminobenzolsul- fonamido)-benzolsulfondimethylamid ist neu. Es bildet nach dem Umkristallisieren aus ver dünntem Alkohol farblose Kristalle vom Schmelzpunkt 194'. Es soll therapeutische Anwendung finden.
Beispiel: 10 g 4@(4'-Azobenzolsulfonamido)-benzol- sulfondimethylamid (dargestellt durch Kon densation von Azobenzol-4-sulfochlorid mit 4-Aminobenzolsulfondimethylamid in Pyri- din, durch Umkristallisation aus verdünntem Alkohol rötlichgelbe Kristalle vom Schmelz punkt 181 ) werden in wässriger Natron lauge gelöst und so lange festes Natrium- hydrosulfit unter schwachem Erwärmen zu,
- gesetzt, bis die Lösung dauernd entfärbt ist. Durch Ansäuern der Lösung mit Essigsäure wird das 4-(4'-Aminobenzolsulfonamido)-ben- zolsulfondimethylamid ausgefällt, das nach Umkristallisieren aus verdünntem Alkohol farblose Kristalle vom Schmelzpunkt 194' bildet. Die Reduktion der Azoverbindung kann man auch mit milder wirkenden Reduk tionsmitteln, zum Beispiel Natriumamalgam oder Zinkstaub, zur entsprechenden Hydrazo- verbindung führen und diese wie oben wei ter reduzieren.
Process for preparing an aminobenzenesulfonic acid amide compound. According to the invention described in patent 199315, certain aminoacyl- and ogyacyl-aminobenzenesulfonic acid amides and their substitution products are distinguished by their action against bacterial infectious diseases.
The present patent relates to a process for the preparation of an aminobenzenesulfonic acid amide compound, which is characterized in that 4- (4'-azobenzenesulfonamido) -benzenesulfon-dimethylamide is reduced to 4- (4'-aminobenzenesulfonamido) -benzenesulfonedimethylamide. The reduction is expediently carried out using sodium hydrosulphite in an aqueous-alkaline solution.
The reduction product can be separated from the alkaline reaction mixture by acidification with acetic acid. The first step in the reduction is 4-4'-hydrazobenzenesulfonamido) -benzenesulfonedimethylamide, which is usually further reduced to the end product without further ado. If milder reducing agents are used, the hydrazo compound mentioned can be found in the reaction mixture; it is then converted into the end product by more powerful reducing agents.
The 4- (4'-aminobenzenesulfonamido) -benzenesulfonedimethylamide obtainable in this way is new. After recrystallization from dilute alcohol, it forms colorless crystals with a melting point of 194 '. It should find therapeutic application.
Example: 10 g of 4 @ (4'-azobenzenesulfonamido) -benzenesulfondimethylamide (produced by condensation of azobenzene-4-sulfochloride with 4-aminobenzenesulfonedimethylamide in pyridine, reddish yellow crystals with a melting point of 181 by recrystallization from dilute alcohol) dissolved aqueous sodium hydroxide solution and add solid sodium hydrosulphite with gentle heating,
- set until the solution is permanently discolored. By acidifying the solution with acetic acid, the 4- (4'-aminobenzenesulfonamido) -benzenesulfondimethylamide is precipitated, which after recrystallization from dilute alcohol forms colorless crystals with a melting point of 194 '. The reduction of the azo compound can also lead to the corresponding hydrazo compound with milder reducing agents, for example sodium amalgam or zinc dust, and this can be further reduced as above.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE207675X | 1936-02-06 | ||
| CH204383T | 1937-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207675A true CH207675A (en) | 1939-11-15 |
Family
ID=25724056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207675D CH207675A (en) | 1936-02-06 | 1937-01-12 | Process for preparing an aminobenzenesulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207675A (en) |
-
1937
- 1937-01-12 CH CH207675D patent/CH207675A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH207674A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| AT140943B (en) | Process for obtaining pure ergot alkaloids from the mixture of total alkaloids and in particular for obtaining a new ergot alkaloid. | |
| CH232273A (en) | Process for the production of a cyclopentano-dimethyl-polyhydro-phenanthrene-carboxylic acid. | |
| CH204383A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| DE727404C (en) | Process for the production of betaine-like constituted condensation products | |
| DE954595C (en) | Process for the production of fungicides and insect repellants of the crotonic acid amide and ª ‰ -Methylcrotonic acid amide series | |
| DE704297C (en) | Process for the preparation of neutral, oil-soluble and sterilizable organic bismuth salts | |
| DE539806C (en) | Process for the preparation of isopropylallylbarbituric acid | |
| DE848650C (en) | Process for the preparation of 3-substituted AEtiocholensaeurederivaten | |
| DE500162C (en) | Process for the preparation of 4-methyl-6-halogen-3-oxy-1-thionaphthenes | |
| AT219204B (en) | Process for the preparation of 3-alkoxy-19-nor-δ <2,5 (10)> -androstadien-17-one | |
| DE164366C (en) | ||
| DE669809C (en) | Process for the preparation of sulphonic acids of 5-oxyacenaphthene | |
| DE473519C (en) | Procedure for the representation of ureides | |
| DE844149C (en) | Process for the preparation of aromatic oxycarboxylic acid arylides | |
| CH194876A (en) | Process for the preparation of 2 (3 ', 5'-Diiodo-2'-B-oxethyl-4'-oxypheny) - 6-iodoquinoline-4-carboxylic acid. | |
| DE1000382B (en) | Process for the preparation of theophylline-7-acetic acid and its derivatives | |
| CH245838A (en) | Process for the preparation of an araliphatic amine. | |
| CH239147A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH193541A (en) | Method for the preparation of 17-ethyl-dihydro-follicle hormone. | |
| CH206631A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH119226A (en) | Process for the preparation of 2-amino-5-iodopyridine. | |
| DE1090207B (en) | Process for the preparation of water-soluble corticosteroid derivatives | |
| DE1136715B (en) | Process for the preparation of 4,4'-dihydroxy-2 "-amino-triphenylmethane and its derivatives | |
| DE1144289B (en) | Process for the preparation of 3-oxo-spiro- (cycloalkane-1 ', 2-coumarans) |