CH253173A - 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
- CH253173A CH253173A CH253173DA CH253173A CH 253173 A CH253173 A CH 253173A CH 253173D A CH253173D A CH 253173DA CH 253173 A CH253173 A CH 253173A
- Authority
- CH
- Switzerland
- Prior art keywords
- butyl
- saponification
- radical
- amino
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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)
Description
Verfahren zur Herstellung eines acylierten p-Amino-benzolsulfonami Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylierten p- Ainino-benzolsulfonamides. Das Verfahren ist dadurch gekennzeichnet,
da.ss man eine Verbindun- der Formel
EMI0001.0009
auf eine Verbindung der Formel
EMI0001.0010
worin X und Y zwei bei der Reaktion mit A.usnahine einer in einem von ihnen enthal tenen NII-Gruppe sich abspaltende Reste und R einen durch Verseifung in die Amino- gruppe überführbaren Rest, wie z. B. eine a.eylainino- oder Carbalkoxyaminogruppe, bedeuten, einwirken lässt und in der erhalte nen.
Verbindung den Rest R durch Versei- fung in die Aminogruppe überführt.
Die neue Verbindung, das 4-Amiiio-benzol- sulfan -N1- [ 5'-tertiärbuty 1-f uran-ca i,bonsiiui-e- ( 2')@-ainid, bildet farblose Kristalle vom Schmelzpunkt<B>239'.</B> Sie lässt sich mit anorga nischen und organischen Basen in Salze über führen. Sie soll therapeutische Verwendung finden.
<I>Beispiel:</I> <B>2-3</B> Teile 4-Carbomethoxyamino-benzolsul- fonamid werden in 100 Teilen Chlorbenzol finit 7 3 Teilen 5-Tertiärbutyl-fura.nea.rbon- säure-(2)-chlorid und 1 Teil Kupferpulver 6 Stunden unter Rückfluss erhitzt.
Nach be endeter Salzsäureentwicklung wird das Chlor benzol mit Wasserda.m2f abdestilliert, der Rückstand in Sodalösung aufgenommen, fil triert und mit Salzsäure das 4-Carbometh- oxyamino-,benzolsulfon-N,- [5'-tertiärbutyl- furan-carbonsäure-(2')]-amid ausgefällt.
Mit verdünnter Natronlauge 1 Stunde auf dem Wasserbad erhitzt entsteht das 4-Amino- benzolsulfon-Nl- [5'-tertiärbutyl-furan-car- bonsäure-(2')]-amid-Natrium, das nach An säuern und Umkristallisieren das freie Sul fonamid vom Schmelzpunkt 2ä9 liefert. Die oben genannten Ausgangskörper lassen sich auch in andern als dem angege benen Mengenverhältnis, z. B. mit. einem Ü berschuss an Säurechlorid oder Benzolsul- fonamid, anwenden.
Man kann die Kondensation des 4-Carbo- methoxyamino-benzolsulfonamides mit 5-Ter- tiärbutyl-furancarbonsäure-(2)-chlorid an statt in Chlorbenzol unter Zusatz von Kupfer pulver, z. B. auch in Nitrobenzol unter Zu satz von Aluminiumchlorid, in Chlorbenzol unter Zusatz von oalcinierter Soda oder in Pyridin durchführen.
Ebensogut kann man von einer Metallverbindung des 4-Carbometh- oxyamino-benzolsulfonamides ausgehen und diese mit 5-Tertiärbutyl-furancarbonsäure- (2)-chlorid umsetzen. Ferner kann man 4-Carbomethoxyamino-benzolsulfonamid auch mit 5-Tertiärbutyl-furanearbonsäure-(2) in Gegenwart von Kondensationsmitteln, z. B. von Phosphorpentssxyd oder von Phosphor- pentachlorid umsetzen.
Zum gleichen Endprodukt gelangt mau auch, wenn man eine Metallverbindung des 5-Tertiärbutyl-furancarbonsäure- (2) -amides mit einem 4-Carbomethoxyamino-benzolsulfo- halogenid umsetzt und die erhaltene Carbo- methoxyverbindung verseift.
An Stelle des Carbomethoxyamino- benzolsulfonamides lässt sich auch das 4-Acetylamino-benzolsulfonamid als Aus gangsmaterial benützen.
Process for the preparation of an acylated p-amino-benzenesulfonamide The present patent is a process for the preparation of an acylated p-amino-benzenesulfonamide. The procedure is characterized by
there is a compound and the formula
EMI0001.0009
to a compound of the formula
EMI0001.0010
where X and Y are two radicals which split off in one of them contained NII group in the reaction with A.usnahine and R is a radical which can be converted into the amino group by saponification, such as, for. B. an a.eylainino- or Carbalkoxyaminogruppe, mean, can act and receive in the NEN.
Compound, the radical R is converted into the amino group by saponification.
The new compound, 4-amino-benzenesulfane -N1- [5'-tertiary-buty-1-furan-ca i, bonsiiui-e- (2 ') @-ainide, forms colorless crystals with a melting point of <B> 239' . </B> It can be converted into salts with inorganic and organic bases. It should find therapeutic use.
<I> Example: </I> <B> 2-3 </B> parts of 4-carbomethoxyamino-benzenesulfonamide are converted into 100 parts of chlorobenzene finitely 7 3 parts of 5-tert-butyl-fura.nea.rbon- acid- (2 ) chloride and 1 part of copper powder heated under reflux for 6 hours.
After the evolution of hydrochloric acid has ended, the chlorobenzene is distilled off with waterda.m2f, the residue is taken up in soda solution, filtered and the 4-carbomethoxyamino-, benzenesulfon-N, - [5'-tert-butyl-furan-carboxylic acid- (2 ')] - amide precipitated.
When heated with dilute sodium hydroxide solution on a water bath for 1 hour, the 4-aminobenzenesulfone-Nl- [5'-tert-butyl-furan-carboxylic acid- (2 ')] amide-sodium is formed, which after acidification and recrystallization the free Sul formamide with a melting point of 2-9. The above starting bodies can also be used in other than the specified quantity ratio, eg. B. with. an excess of acid chloride or benzenesulfonamide.
You can use the condensation of 4-carbomethoxyamino-benzenesulfonamides with 5-tert-butyl-furancarboxylic acid (2) chloride instead of in chlorobenzene with the addition of copper powder, eg. B. also in nitrobenzene with the addition of aluminum chloride, in chlorobenzene with the addition of soda ash or in pyridine.
One can just as well start from a metal compound of 4-carbomethoxyamino-benzenesulfonamide and react it with 5-tert-butyl-furancarboxylic acid (2) chloride. You can also 4-carbomethoxyamino-benzenesulfonamide with 5-tert-butyl-furanearboxylic acid (2) in the presence of condensing agents, eg. B. of phosphorus pentachloride or of phosphorus pentachloride.
The same end product is also obtained when a metal compound of 5-tert-butyl-furancarboxylic acid (2) amide is reacted with a 4-carbomethoxyamino-benzenesulfohalide and the resulting carbomethoxy compound is saponified.
Instead of the carbomethoxyamino-benzenesulfonamide, 4-acetylamino-benzenesulfonamide can also be used as the starting material.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH222076T | 1943-05-06 | ||
| CH253173T | 1943-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253173A true CH253173A (en) | 1948-02-15 |
Family
ID=25726597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253173D CH253173A (en) | 1943-05-06 | 1943-11-05 | Process for the preparation of an acylated p-amino-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253173A (en) |
-
1943
- 1943-11-05 CH CH253173D patent/CH253173A/en unknown
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