CH211297A - Process for the preparation of phosphoric acid dichloride-4-sulfonamidoanilide. - Google Patents
Process for the preparation of phosphoric acid dichloride-4-sulfonamidoanilide.Info
- Publication number
- CH211297A CH211297A CH211297DA CH211297A CH 211297 A CH211297 A CH 211297A CH 211297D A CH211297D A CH 211297DA CH 211297 A CH211297 A CH 211297A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonamidoanilide
- phosphoric acid
- acid dichloride
- preparation
- phosphorus oxychloride
- Prior art date
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 17
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 16
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 229950000244 sulfanilic acid Drugs 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 101000701936 Homo sapiens Signal peptidase complex subunit 1 Proteins 0.000 claims 1
- 102100030313 Signal peptidase complex subunit 1 Human genes 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Phosphorsänredichlorid-4-sulfonamidoanilid. Es wurde gefunden, dass 4-Aminobenzol- sulfonamide der allgemeinen Formel
EMI0001.0004
worin R Alkyl oder Wasserstoff, R, Alkyl, Aryl oder Wasserstoff und R2 Alkyl oder Wasserstoff bedeuten, beim Erhitzen mit Phosphoroxychlorid in Dichloride substi tuierter Phosphorsäuren der allgemeinen Formel
EMI0001.0013
übergehen.
Die 4-Aminobenzolsulfonamide können als solche oder in Form ihrer Salze zur Reaktion gebracht werden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Phosphor säuredichlorid-4-sulfonamidoanilid, welches dadurch gekennzeichnet ist, dass Sulfanil- säureamid mit Phosphoroxychlorid erhitzt wird. Man kann dabei das Sulfanilsäureamid auch in Form seiner Salze verwenden.
Das Phosphorsäuredichlorid - 4 - sulfon- amidoanilid C,H703N2SPCl, bildet ein wenig gefärbtes Pulver, das heftig mit Laugen oder Ammoniak unter Abspaltung von 2 Mol Salz säure reagiert.
Die entstehende Phosphamid- säure ist alkalilöslich. Das neue Phosphor- säuredichlorid-4-sulfonamidoanilid bildet ein Zwischenprodukt für die Herstellung von bakterizid wirkenden, leicht löslichen, inji- zierbaren Arzneimitteln.
Beispiel <I>1:</I> 40 Teile Sulfanilsäureamid-hydrochlorid werden 2 Stunden mit 100 Teilen Phosphor- oxychlorid am Rückflusskühler gekocht. Es tritt starke Salzsäureentwicklung ein, und nach etwa 1 Stunde ist eine klare, dünnflüs sige Lösung entstanden. Diese heisse Lösung wird in 200 Teile Benzol eingerührt, wobei überschüssiges Phosphoroxychlorid in Lö sung geht und das Reaktionsprodukt erstarrt. Es wird nochmals mit 100 Teilen Benzol verrieben, um den Rest des Phosphoroxychlo- rids zu entfernen.
Beispiel <I>2:</I> 30 Teile Sulfanilsäureamid erden mit 100 Teilen Phosphoroxychlorid 3 bis 4 Stun den am Rückflusskühler zum Sieden erhitzt. Die Aufarbeitung erfolgt durch Eingiessen der Reaktionslösung in ein Gemisch von Benzol und Petroläther oder durch Abdamp fen des überschüssigen Phosphoroxychlorids im Vakuum. Man erhält das Phosphorsäure- dichlorid-4-sulfonamidoa.nilid wie im Bei spiel 1.
Process for the preparation of phosphorus acid dichloride-4-sulfonamidoanilide. It was found that 4-aminobenzenesulfonamides of the general formula
EMI0001.0004
where R is alkyl or hydrogen, R, alkyl, aryl or hydrogen and R2 is alkyl or hydrogen, phosphoric acids of the general formula substituted in dichlorides on heating with phosphorus oxychloride
EMI0001.0013
pass over.
The 4-aminobenzenesulfonamides can be reacted as such or in the form of their salts.
The subject of the present patent is a process for the preparation of phosphoric acid dichloride-4-sulfonamidoanilide, which is characterized in that sulfanilic acid amide is heated with phosphorus oxychloride. The sulfanilic acid amide can also be used in the form of its salts.
The phosphoric acid dichloride - 4 - sulfonamidoanilide C, H703N2SPCl, forms a slightly colored powder that reacts violently with alkalis or ammonia, splitting off 2 mol of hydrochloric acid.
The resulting phosphamic acid is soluble in alkali. The new phosphoric acid dichloride-4-sulfonamidoanilide forms an intermediate product for the manufacture of bactericidal, easily soluble, injectable drugs.
Example <I> 1 </I> 40 parts of sulfanilic acid amide hydrochloride are boiled for 2 hours with 100 parts of phosphorus oxychloride in a reflux condenser. There is strong evolution of hydrochloric acid, and after about 1 hour a clear, thin liquid solution has formed. This hot solution is stirred into 200 parts of benzene, excess phosphorus oxychloride going into solution and the reaction product solidifying. It is triturated again with 100 parts of benzene in order to remove the remainder of the phosphorus oxychloride.
Example <I> 2: </I> 30 parts of sulfanilic acid amide ground with 100 parts of phosphorus oxychloride for 3 to 4 hours on the reflux condenser. Working up is carried out by pouring the reaction solution into a mixture of benzene and petroleum ether or by evaporating the excess phosphorus oxychloride in vacuo. The phosphoric acid dichloride-4-sulfonamidoa.nilid is obtained as in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE211297X | 1938-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211297A true CH211297A (en) | 1940-09-15 |
Family
ID=5801893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211297D CH211297A (en) | 1938-05-16 | 1939-04-18 | Process for the preparation of phosphoric acid dichloride-4-sulfonamidoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211297A (en) |
-
1939
- 1939-04-18 CH CH211297D patent/CH211297A/en unknown
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