CH206631A - Process for preparing an aminobenzenesulfonic acid amide compound. - Google Patents
Process for preparing an aminobenzenesulfonic acid amide compound.Info
- Publication number
- CH206631A CH206631A CH206631DA CH206631A CH 206631 A CH206631 A CH 206631A CH 206631D A CH206631D A CH 206631DA CH 206631 A CH206631 A CH 206631A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid amide
- amide compound
- preparing
- aminobenzenesulfonic acid
- ammonia
- Prior art date
Links
- -1 aminobenzenesulfonic acid amide compound Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent 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 Aminobenzolsulfonsäureamidverbindnng. Gemäss der im Patent Nr.19931ä be schriebenen Erfindung sind gewisse Amino- acyl- und Ogyacylaminobenzolsulfonsäure- amide sowie deren Substitutionsprodukte durch ihre Wirkung gegen bakterielle Infek tionskrankheiten ausgezeichnet.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer Amino- benzolsulfonsäureamidverbindung, welches da durch gekennzeichnet ist, dass man auf ein 4-(4'.Halogeiibenzolsulfonamido)-benzolsulfon- monomethylamid bei erhöhter Temperatur und erhöhtem Druck Ammoniak einwirken lässt. Die Umsetzung erfolgt zweckmässig in einem Lösemittel wie Wasser, Methyl- oder Äthylalkohol. Vorteilhaft verwendet man das 4-(4'-Brombenzolsulfonamido) - benzolsulfon- monomethylamid. Das Reaktionsprodukt lässt sich aus der Reaktionsmischung in an sich üblicher Weise, z.
B, durch Eindampfen der Mischung, Lösen des Rückstandes in ver dünntem Alkali und Ausfällen des Reak- tionsproduktes, z. B. mit verdünnter Essig säure, abscheiden. Nach dem Umkristallisieren, z. B. aus Alkohol, bildet das so erhältliche 4 - (4'-Aminobenzolsulfonamido) -benzolsulfon- monomethylamid farblose Kristalle vom Schmelzpunkt 141 . Es ist in kaltem Wasser schwer löslich, löslich in verdünnten Alkalien und soll therapeutische Anwendung finden.
<I>Beispiel:</I> 20 g 4-(4'-Brombenzolsulfonamido)-benzol- sulfonmonomethylamid (dargestellt durch Kondensation von 4-Brombenzolsulfochlorid mit 4-Aminobenzolsulfonmonomethylamid in Pyridin, aus verdünntem Alkohol farblose Kristalle vom Schmelzpunkt<B>1880)</B> werden im Rührautoklaven mit 120 cm' konzen triertem wässrigen Ammoniak 10 Stunden auf 2000 bei etwa 60-70 Atmosphären Druck erhitzt. Die Reaktionsmischung wird unter vermindertem Druck auf dem Wasserbade zur Trockne gebracht, mit verdünnter Natron- lauge gelöst, filtriert und mit Essigsäure an gesäuert.
Das ausgefallene 4-(4'-Arnirroberrzol- sulfonamido)-benzolsulfonmonomethylamid bil. det nach dem Umkristallisieren aus verdünn tem Alkohol farblose Kristalle vom Schmelz punkt 141 . AnStellevonwässrigemAmmoniak kann man auch methylalkoholisches oder äthylalkoholisches Ammoniak<B>zur</B> Umsetzung verwenden. An Stelle der Bromverbindung können auch andere Halogenverbindungen, z. B. die Jod- oder die Chlorverbindung, Anwendung finden. Bei der Chlorverbindung wird die Reaktionstemperatur zweckmässig etwas erhöht.
Process for the preparation of an aminobenzenesulfonic acid amide compound. According to the invention described in patent no.19931ä, certain aminoacyl- and ogyacylaminobenzenesulfonic acid amides and their substitution products are distinguished by their action against bacterial infectious diseases.
The subject matter of the present patent is a process for the preparation of an aminobenzenesulfonic acid amide compound, which is characterized in that ammonia is allowed to act on a 4- (4'.halogeiibenzenesulfonamido) -benzenesulfonamethylamide at elevated temperature and pressure. The reaction is conveniently carried out in a solvent such as water, methyl or ethyl alcohol. It is advantageous to use 4- (4'-bromobenzenesulfonamido) -benzenesulfonmonomethylamide. The reaction product can be extracted from the reaction mixture in a conventional manner, e.g.
B, by evaporating the mixture, dissolving the residue in ver dilute alkali and precipitating the reaction product, eg. B. with dilute acetic acid, deposit. After recrystallization, e.g. B. from alcohol, the so obtainable 4 - (4'-aminobenzenesulfonamido) -benzenesulfonmonomethylamide forms colorless crystals with a melting point of 141. It is sparingly soluble in cold water, soluble in dilute alkalis and is said to be of therapeutic use.
<I> Example: </I> 20 g of 4- (4'-bromobenzenesulfonamido) -benzenesulfonmonomethylamide (produced by the condensation of 4-bromobenzenesulfonyl chloride with 4-aminobenzenesulfonomethylamide in pyridine, from dilute alcohol colorless crystals with a melting point of <B> 1880) </B> are heated in a stirred autoclave with 120 cm 'concentrated aqueous ammonia for 10 hours to 2000 at about 60-70 atmospheric pressure. The reaction mixture is brought to dryness on a water bath under reduced pressure, dissolved with dilute sodium hydroxide solution, filtered and acidified with acetic acid.
The precipitated 4- (4'-Arnirroberrzol- sulfonamido) -benzolsulfonmonomethylamid bil. after recrystallization from dilute alcohol, colorless crystals with a melting point of 141. Instead of aqueous ammonia, methyl alcoholic or ethyl alcoholic ammonia can also be used for the reaction. Instead of the bromine compound, other halogen compounds, e.g. B. the iodine or the chlorine compound find application. With the chlorine compound, the reaction temperature is expediently increased somewhat.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE206631X | 1936-02-06 | ||
| CH204380T | 1937-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206631A true CH206631A (en) | 1939-08-15 |
Family
ID=25724049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206631D CH206631A (en) | 1936-02-06 | 1937-01-12 | Process for preparing an aminobenzenesulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206631A (en) |
-
1937
- 1937-01-12 CH CH206631D patent/CH206631A/en unknown
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