CH253169A - Process for the preparation of a p-amino-benzene-sulfonacylamide. - Google Patents
Process for the preparation of a p-amino-benzene-sulfonacylamide.Info
- Publication number
- CH253169A CH253169A CH253169DA CH253169A CH 253169 A CH253169 A CH 253169A CH 253169D A CH253169D A CH 253169DA CH 253169 A CH253169 A CH 253169A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- compound
- amino
- radical
- saponification
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- 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
- 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- -1 sulfo halide Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 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
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-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
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring 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
-
- 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
<B>Verfahren</B> zur <B>Herstellung eines</B> p-Amino-benzol-sulfonacylamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylierten p-Amino-benzolsulfonamides. Das Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI0001.0005
auf eine Verbindung der Formel
EMI0001.0006
worin X und Y zwei bei der Reaktion mit Ausnahme einer in einem von ihnen enthal tenen NH-Gruppe sich abspaltende Reste und R einen durch Verseifung in die Amino- gruppe überführbaren Rest bedeuten,
ein wirken lässt und in der erhaltenen Verbin dung den Rest R durch Verseifung in die Aminogruppe überführt.
Die entstandene neue Verbindung, das 17-A.mino-benzolsulfon-N,,- [a,a-Dimethyl-a- (3,4-dimethyl-benzyl)-acetyl]-amid, bildet farblose Kristalle vom Schmelzpunkt 173 bis 174 . Sie lässt sich mit anorganischen oder organischen Basen in Salze überführen. Sie soll therapeutische Verwendung finden. <I>Beispiel:</I> 112 Teile a,a-Dimethyl-a-(3,4-dimethyl- benzyl)-essigSäureehlorid werden mit 250 Teilen Chlorbenzol, 2 Teilen Kupferpulver und 107 Teilen p-Acetylamino-benzolsulfon- amid über Nacht am Rückfluss erhitzt.
Die Reaktionsmasse wird in warme, verdünnte Sodalösung unter gutem Rühren eingetragen und nach dem Erkalten filtriert. Das Filtrat wird vom Chlorbenzol befreit und angesäuert. Die rohe, aus Sodalösung umgefällte Acetyl- verbindung wird mit 40 Teilen Natrium hydrogyd in 250 Teilen Wasser 1 Stunde am Rückfluss erhitzt.
Nach dem Verdünnen mit Wasser wird mit Tierkohle geschüttelt, fil triert und angesäuert, wobei das p-Amino- benzolsulfon - N, - [a,a - dimethyl - a -1 (3,4 - di- methyl-benzyl)-acetyl]-amid ausfällt. Nach Umfällen aus Sodalösung lässt sich die neue Verbindung durch Umkristallisieren aus ver dünntem Alkohol rein erhalten und schmilzt dann bei 173-174 .
Man kann die Kondensation des p-Acetyl- amino-benzolsulfonamides mit a,a-Dimethyl- a-(3,4-dimethyl-benzyl)-essigsäurechlorid an statt in Chlorbenzol auch in Nitrobenzol unter Zusatz von Aluminiumchlorid oder in Pyridin durchführen. Ebensogut kann man von einer Metallverbindung des p-Acetyl- amino-benzolsulfonamides ausgehen und diese mit a,a-Dimethyl-a-(3,4-dimethyl-benzyl)- essigsäureehlorid umsetzen.
Ferner kann man p-Acetylamino-benzolsulfonamid auch mit a,a-Dimethyl -,a- (3,4-dimethyl-benzyl)-essig- säure in Gegenwart von Kondensationsmit- teln, z. B. von Phosphorpentogyd oder von Phosphorpentachlorid, umsetzen.
Zum gleichen Endprodukt gelangt man auch, wenn man eine Metallverbindung des a,a -Dimethyl - a -(3,4-dimethyl-benzyl)-essig- säureamides mit einem p-Acetylamino-benzol- sulfonhalogenid umsetzt und die erhaltene Acetylverbindung verseift.
<B> Process </B> for the <B> production of </B> a p-amino-benzene-sulfonacylamide. The present patent is a process for the preparation of an acylated p-amino-benzenesulfonamide. The process is characterized in that a compound of the formula
EMI0001.0005
to a compound of the formula
EMI0001.0006
in which X and Y are two radicals which split off in the reaction with the exception of one of them contained in an NH group and R is a radical which can be converted into the amino group by saponification,
A can act and in the compound obtained the radical R is converted into the amino group by saponification.
The resulting new compound, 17-A.mino-benzenesulfon-N ,, - [a, a-Dimethyl-a- (3,4-dimethyl-benzyl) -acetyl] -amide, forms colorless crystals with a melting point of 173 to 174 . It can be converted into salts with inorganic or organic bases. It should find therapeutic use. <I> Example: </I> 112 parts of a, a-dimethyl-a- (3,4-dimethylbenzyl) acetic acid chloride are mixed with 250 parts of chlorobenzene, 2 parts of copper powder and 107 parts of p-acetylamino-benzenesulphonamide Heated to reflux overnight.
The reaction mass is introduced into warm, dilute soda solution with thorough stirring and, after cooling, filtered. The filtrate is freed from chlorobenzene and acidified. The crude acetyl compound, which has been reprecipitated from soda solution, is refluxed with 40 parts of sodium hydroxide in 250 parts of water for 1 hour.
After dilution with water, it is shaken with animal charcoal, filtered and acidified, whereby the p-aminobenzenesulfone - N, - [a, a - dimethyl - a -1 (3,4 - dimethylbenzyl) acetyl] -amid fails. After reprecipitation from soda solution, the new compound can be obtained in pure form by recrystallization from dilute alcohol and then melts at 173-174.
The condensation of p-acetylamino-benzenesulfonamide with a, a-dimethyl-a- (3,4-dimethyl-benzyl) acetic acid chloride can also be carried out in nitrobenzene with the addition of aluminum chloride or in pyridine instead of in chlorobenzene. One can just as well start from a metal compound of p-acetylamino-benzenesulfonamide and react this with a, a-dimethyl-a- (3,4-dimethyl-benzyl) acetic acid chloride.
Furthermore, p-acetylamino-benzenesulfonamide can also be used with a, a-dimethyl-, a- (3,4-dimethyl-benzyl) -acetic acid in the presence of condensing agents, e.g. B. of phosphorus pentogyd or phosphorus pentachloride, implement.
The same end product is also obtained if a metal compound of α, α-dimethyl-α- (3,4-dimethyl-benzyl) -acetic acid amide is reacted with a p-acetylamino-benzenesulfone halide and the resulting acetyl compound is saponified.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH219520T | 1940-06-21 | ||
| CH253169T | 1943-09-14 | ||
| CH242285T | 1943-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253169A true CH253169A (en) | 1948-02-15 |
Family
ID=34139167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253169D CH253169A (en) | 1940-06-21 | 1943-09-14 | Process for the preparation of a p-amino-benzene-sulfonacylamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253169A (en) |
-
1943
- 1943-09-14 CH CH253169D patent/CH253169A/en unknown
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