CH264507A - Process for the preparation of an acylated p-amino-benzenesulfonamide. - Google Patents
Process for the preparation of an acylated p-amino-benzenesulfonamide.Info
- Publication number
- CH264507A CH264507A CH264507DA CH264507A CH 264507 A CH264507 A CH 264507A CH 264507D A CH264507D A CH 264507DA CH 264507 A CH264507 A CH 264507A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- saponification
- formula
- radical
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 238000007127 saponification reaction Methods 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- -1 carbethoxy compound Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 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
-
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines acylierten p-Amino-benzolsulfonamids. Gegenstand vorliegenden Patentes ist ein Verfahren zur Verstellung eines aeylierten p-Airiino-henzolsulfonamids. Das Verfahren ist dadurch gekennzeichnet., dass man eine Verbindung der Formel
EMI0001.0005
auf eine Verbindun- der Formel
EMI0001.0007
worin X und Y zwei bei der Reaktion mit Ausnahme einer in einem von ihnen enthal tenen NI1-Gruppe sich abspaltende Reste und R einen durch Verseifimg in die Aminogruppe überführbaren Rest., wie z.
B. eine Acvlamino- oder Carbalkoxyaniino-Gruppe, bedeuten, ein wirken lässt und in der erhaltenen Verbin- dlulg den Rest R. dureh Verseifung in die Aminogrul>pe überführt.
Die entstandene neue Verbindung, das p- Amino - bc,n7o]sulfon-iNT,-(a-n-propoxy-l)ropio- nylj-ami < 1, bildet farblose Kristalle vom Schmelzpunkt 140". Sie lässt sich mit anor- ganisehen oder org-anisehen Basen in Salze überführen. Sie soll therapeutische Verwen dung finden.
Beispiel: 24,4 Teile p-Carbäthoxyamino - henzolsul- fonamid werden in Chlorbenzol mit<B>15</B> Teilen a-n-1'i-olioxy-propionsäurecllloricl und 2 Tei len Kupferpulver versetzt und das Gemiseh einige Stunden zum Sieden erhitzt.
Nacll- her wird das Chlorbenzol mit Wasserdampf abdestilliert, der Rückstand in Sodalösung <B>,</B> auin genommen, filtriert und das Filtrat mit Salzsäure versetzt.
Die Carbäthoxy verbin- clung wird mit verdünnter Natronlauge ver seift und das entstandene p Amino-benzolsul- fon-N1-(a-n-propoxy-propionyl) - amid durch Umkristallisation aus Alkohol gereinigt, wor auf es einen Schmelzpunkt von 140 zeigt.
-Man kann die Kondensation des p-Carb- iithoxyanlillo - benzolsulfonamids mit a-Prop- oxy-propionsäurechlorid anstatt in Chlorben zol.
auch in Nitrobenzol unter Zusatz von Aluminiumchlorid oder in Py ridin dureli- führen. Ebensogut Bann man von einer Me tallverbindung des p-Carbäthoxyamino - ben- zolsulfonaniids ausgehen und diese mit a-n- Propoxy-propionsäureehlorid umsetzen. Fer ner kann man p-Carhäthoxyaniino-benzolsul- fonainid auch mit a-n-Propoxy-propionsäure in Gegenwart von Kondensationsmitteln, z. B.
von Phosphorpentoxyd oder von Phosphor- pentaehlorid, umsetzen.
Zum gleichen Endprodukt gelangt man auch, wenn man eine Metallverbindung des a- n-Propoxy-propionsäureamids mit einem p Carbäthox5 amino - benzolsulfolialogenid um setzt und die erhaltene Carbäthoxy-verbindung verseift.
Process for the preparation of an acylated p-amino-benzenesulfonamide. The subject of the present patent is a process for adjusting an aylated p-Airiino-henzenesulfonamide. The process is characterized in that one has a compound of the formula
EMI0001.0005
on a compound of the formula
EMI0001.0007
wherein X and Y are two residues which split off in the reaction with the exception of one in one of them contained NI1 group and R is a residue which can be converted into the amino group by saponification.
B. an Acvlamino- or Carbalkoxyaniino group, mean, lets act and in the compound obtained the remainder R is converted into the amino group by saponification.
The resulting new compound, the p-amino-bc, n7o] sulfone-iNT, - (an-propoxy-1) ropionylj-ami <1, forms colorless crystals with a melting point of 140 ". It can be seen with inorganic or Conversion of organic bases into salts for therapeutic use.
Example: 24.4 parts of p-carbethoxyamino-henzenesulfonamide are mixed in chlorobenzene with 15 parts of a-n-1'i-olioxy-propionic acid chloricl and 2 parts of copper powder and the mixture is heated to the boil for a few hours.
The chlorobenzene is then distilled off with steam, the residue is taken up in soda solution, filtered and the filtrate is treated with hydrochloric acid.
The carbethoxy compound is soaped with dilute sodium hydroxide solution and the resulting p-amino-benzenesulfon-N1- (a-n-propoxypropionyl) amide is purified by recrystallization from alcohol, whereupon it has a melting point of 140.
- You can use the condensation of p-Carb- iithoxyanlillo - benzenesulfonamide with a-Propoxy-propionic acid chloride instead of in chlorobenzene.
also lead in nitrobenzene with the addition of aluminum chloride or in pyridine dureli. It is just as good to start from a metal compound of p-carbethoxyamino - benzene sulfonaniids and react this with a-n-propoxypropionic acid chloride. Fer ner can p-Carhäthoxyaniino-benzenesulfonainid with a-n-propoxy-propionic acid in the presence of condensing agents, eg. B.
of phosphorus pentoxide or of phosphorus penta chloride.
The same end product is also obtained if a metal compound of a-n-propoxypropionic acid amide is reacted with a p carbethox5amino-benzenesulfolialogenide and the resulting carbethoxy compound is saponified.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH219520T | 1940-06-21 | ||
| CH264507T | 1943-11-05 | ||
| CH242285T | 1943-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264507A true CH264507A (en) | 1949-10-15 |
Family
ID=34139175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264507D CH264507A (en) | 1940-06-21 | 1943-11-05 | Process for the preparation of an acylated p-amino-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264507A (en) |
-
1943
- 1943-11-05 CH CH264507D patent/CH264507A/en unknown
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