DE726740C - Process for the production of water-soluble compounds of 4-aminobenzene sulfonamides - Google Patents
Process for the production of water-soluble compounds of 4-aminobenzene sulfonamidesInfo
- Publication number
- DE726740C DE726740C DEH163579D DEH0163579D DE726740C DE 726740 C DE726740 C DE 726740C DE H163579 D DEH163579 D DE H163579D DE H0163579 D DEH0163579 D DE H0163579D DE 726740 C DE726740 C DE 726740C
- Authority
- DE
- Germany
- Prior art keywords
- water
- production
- parts
- soluble compounds
- aminobenzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000009967 tasteless effect Effects 0.000 description 2
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Chemical group Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Verfahren zur Herstellung von wasserlöslichen Abkömmlingen der 4-Anminobenzolsulfonamide Durch das Patent 713 079 wird ein Verfahren zur Herstellung von wasserlöslichen Abkömmlingen der q.-Aminobenzolsulfonamide geschützt, welches dadurch gekennzeichnet ist, daß man auf 4-Am.i.nobenzolsulfonamideder allgemeinen Formel worin R und -Ri Alkyl oder Wasserstoff, R2 Alkyl, Aryl oder Wasserstoff bedeuten, oder auf deren ,Salze Phosphoroxychlorid einwirken läßt und .die dabei entstehenden Monophosphors'äuredichloride mit Ammoniak, Alkylaminen oder Alkalien umsetzt. Die Umsetzung mitPhosphoroxychlorid erfolgt durch Erhitzen. Die erhaltenen Phosphorsäuren bzw. Phosphamidsäuren der q.-Aminobenzolsulfonamide wirken stark bakterizid und sind sehr wenig toxisch. Sie bilden beständige, fast geschmacklose Salze, die leicht löslich sind. Ihre Lösungen reagieren neutral und können sterilisiert und injiziert werden.Process for the preparation of water-soluble derivatives of the 4-aminobenzenesulfonamides The patent 713 079 protects a process for the preparation of water-soluble derivatives of the q-aminobenzenesulfonamides, which is characterized in that one uses 4-aminobenzenesulfonamides of the general formula where R and -Ri are alkyl or hydrogen, R2 is alkyl, aryl or hydrogen, or phosphorus oxychloride is allowed to act on the salts thereof and the resulting monophosphoric acid dichlorides are reacted with ammonia, alkylamines or alkalis. The reaction with phosphorus oxychloride is carried out by heating. The resulting phosphoric acids or phosphamic acids of the q-aminobenzenesulfonamides have a strong bactericidal effect and are very little toxic. They form stable, almost tasteless salts that are easily soluble. Their solutions react neutrally and can be sterilized and injected.
Es wurde nun ,gefunden, daß,dieTJmsetzung der 4.-Aminobenzol,sulfonami.de mit Phosphoroxychlorid auch ohne Erhitzen bei Gegenwart tertiärer, Salzsäure bindender Basen, wie Pyridin, Dialkylanilinen und anderer, vorgenommen werden kann. Die Weiterverarbeitung erfolgt .durch Umsetzung .der rohen oder gereinigten Reaktionsprodukte vor oder nach der Entfernung des tertiären Amins mit Ammoniak, Alkylaminen oder Alkalien.It has now been found that the conversion of the 4th-aminobenzene, sulfonami.de with phosphorus oxychloride even without heating in the presence of tertiary, hydrochloric acid binding Bases such as pyridine, dialkylanilines and others can be made. The further processing takes place .by implementing .the crude or purified reaction products before or after removal of the tertiary amine with ammonia, alkylamines or alkalis.
Beispiel z I5,3 Teile Phosphoroxychlorid werden in 30 Teil-en Benzol gelöst. Unter Kühlung und Rühren läßt man eine Lösung von 17,22 Teilen ¢-Aminobenzolsulfonamid in So Teilen trokkenem Pyridin zutropfen. Die entstandene rote Lösung wird zusammen mit .den festen Anteilen in konzentriertes Ammoniak unter Kühlung eingetragen. Die ammoniakalische Lösung wird :durch Eindampfen im Vakuum vorn Benzol und Pyridin befreit. Beim Ansäuern der wässerigen Lösung fällt die 4-Sulfonamidoanilinphosphamidsäure aus. Man führt sie zur Reinigung in ihr gut kristallisierendes Natriumsalz über. Dieses ist fast geschmacklos, reagiert neutral und kann für therapeutische Zwecke Verwendung finden. Beispiel z 25 Teile Dimethylanilin werden in 25 Teilen Benzol gelöst und unter Kühlung 1 5,3 Teile Phosphoro_xychlorid in 2o Teilen Benzol eingetragen. Dann gibt man portionsweise i7,:2 Teile fein pulverisiertes d. Aminobenzolsulfonamid hinzu und verrührt einige Zeit bei ro bis z5°. Das q.-Aminobenzolsulfoaiami.d setzt sich mit dem Phosphoroxychlorid um, das Reaktionsprodukt bleibt ungelöst.Example z I 5.3 parts of phosphorus oxychloride are dissolved in 30 parts of benzene. With cooling and stirring, a solution of 17.22 parts [-aminobenzenesulfonamide] in 50 parts of dry pyridine is added dropwise. The resulting red solution, together with the solid components, is introduced into concentrated ammonia with cooling. The ammoniacal solution is: freed from benzene and pyridine by evaporation in vacuo. When the aqueous solution is acidified, the 4-sulfonamidoaniline phosphamic acid precipitates. For purification, they are converted into their well-crystallizing sodium salt. This is almost tasteless, reacts neutrally and can be used for therapeutic purposes. Example z 25 parts of dimethylaniline are dissolved in 25 parts of benzene and, with cooling, 1 5.3 parts of phosphoro_xychloride are added to 20 parts of benzene. Then i7: 2 parts of finely powdered d are added in portions. Aminobenzenesulfonamide added and stirred for some time at ro to z5 °. The q.-aminobenzene sulfoaiami.d reacts with the phosphorus oxychloride, the reaction product remains undissolved.
ach Beendigung der Umsetzung gießt man die überstehende b@enzolische Lösung ab und setzt das Reaktionsprodukt unter Kühlung mit i 5o Teilen z 5 °/oigem Ammoniak um. Das abgeschiedene Diinethylanilinentfernt man durch Ausäthern und engt die Lösung zur Entfernung überschüssigen .\nnnoniaks im Vakuum auf die Hälfte ein. \ ach dein Abfiltrieren einer geringen Menge unveränderten 4-Aininobenzolsulfonainids säuert man die Lösung mit überschüssiger Salzsäure .-iii, worauf die im Beispiel t beschriebene -j-Sulfonainidoanilinphosphamiclsäure ausfällt.After the conversion is complete, the protruding B @ enzolian is poured Solution and sets the reaction product with cooling with i 50 parts z 5% Ammonia around. The separated diinethylaniline is removed by etherification and concentrated the solution to remove excess. \ nnnoniaks in a vacuum to half. After filtering off a small amount of unchanged 4-ainobenzene sulfonainide the solution is acidified with excess hydrochloric acid.-iii, whereupon the example t -j-sulfonainidoanilinephosphamiclic acid described precipitates.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEH163579D DE726740C (en) | 1939-03-07 | 1939-03-07 | Process for the production of water-soluble compounds of 4-aminobenzene sulfonamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEH163579D DE726740C (en) | 1939-03-07 | 1939-03-07 | Process for the production of water-soluble compounds of 4-aminobenzene sulfonamides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE726740C true DE726740C (en) | 1942-10-22 |
Family
ID=7183859
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEH163579D Expired DE726740C (en) | 1939-03-07 | 1939-03-07 | Process for the production of water-soluble compounds of 4-aminobenzene sulfonamides |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE726740C (en) |
-
1939
- 1939-03-07 DE DEH163579D patent/DE726740C/en not_active Expired
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