CH253168A - 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
- CH253168A CH253168A CH253168DA CH253168A CH 253168 A CH253168 A CH 253168A CH 253168D A CH253168D A CH 253168DA CH 253168 A CH253168 A CH 253168A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- compound
- dimethyl
- saponification
- radical
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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
- 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
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 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
- 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
- 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 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
- 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt 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
- 230000001376 precipitating effect Effects 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
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 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
verfahren zur Herstellung eines p-Amino-henzol-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
EMI0001.0006
auf eine Verbindung der Formel
EMI0001.0008
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- @'ruppe überführbaren Rest bedeuten, einwir ken lässt und in der erhaltenen Verbindung den Rest R durch Verseifung in die Amino- gruppe überführt.
Die entstandene neue Verbindung, das p-Amino - benzolsulfon - Nx- (ar,@c- Dimethyl-a- benzyl-acetyl)-am:id, bildet farblose Kristalle vom Schmelzpunkt 218 . Sie lä.sst sich mit anorganischen oder organischen Basen in Salze überführen. Sie soll therapeutische Verwendung finden.
<I>Beispiel:</I> 98 Teile a,a <I>-</I> Dimethyl <I>- a</I> - beaizyl - easig- säurechlorid werden mit 250 Teilen Chlor benzol, 2 Teilen Kupferpulver und 107 Teilen p-Acetyl-amino-benzolsulfoiiamid 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 Acetylverbindung wird mit 40 Teilen Natriumhydroxyd in 250 Teilen Wasser 1 Stunde am Rückfluss erhitzt. Nach dem Verdünnen mit Wasser wird mit Tierkohle geschüttelt, filtriert und angesäuert, wobei das p-Amino-benzolsulfon- Nl-(a,a-dimethyl-a-benzyl-acetyl)-amid aus fällt. Nach Umfällen aus Sodalösung lässt sich die neue Verbindung durch Umkristalli- sieren aus verdünntem Alkohol rein erhalten und schmilzt dann bei 218 .
Man kann die Kondensation des p-Acetyl- amino-benzolsulfonamides mit a,a-Dimethyl- a-benzyl-essigsäurechlorid anstatt in Chlor benzol auch in Nitrobenzol unter Zusatz von Aluminiumchlorid oder in Pyridin durchfüh ren. Ebensogut kann man von einer Metall verbindung des p-Acetylamino-benzolsulfon- amides ausgehen und diese mit a@,a-Dimethyl- ä-benzyl-essigsäurechlorid umsetzen.
Ferner kann man p-Acetylamino-benzolsulfonamid auch mit a,a-Dimethyl-a-benzyl-essigsäure in Gegenwart von Kondensationsmitteln, z. B. von Phosphorpentoxyd oder von Phosphor pentachlorid, umsetzen.
Zum gleichen Endprodukt gelangt man auch, wenn man eine Metallverbindung des a,a-Dimethyl-a-benzyl-essigsäureamides mit einem p - Acetylamino - benzolsulfohalogenid umsetzt und die erhaltene Acetylverbindung verseift.
process for the production of a p-amino-henzene-sulfonacylamide. The present patent is a process for the preparation of an acylated p-amino-benzenesulfonamide. The procedure is characterized by
that you can get a compound of the formula
EMI0001.0006
to a compound of the formula
EMI0001.0008
where X and Y are two radicals which split off in the reaction with the exception of one of them contained NH group and R is a radical which can be converted into the amino group by saponification, and the radical R in the compound obtained converted into the amino group by saponification.
The resulting new compound, p-amino-benzenesulphone-Nx- (ar, @ c-dimethyl-a-benzyl-acetyl) -am: id, forms colorless crystals with a melting point of 218. It can be converted into salts with inorganic or organic bases. It should find therapeutic use.
<I> Example: </I> 98 parts a, a <I> - </I> Dimethyl <I> - a </I> - beaizyl - easig- acid chloride are mixed with 250 parts of chlorobenzene, 2 parts of copper powder and 107 Share p-acetyl-amino-benzenesulfoiiamide heated under reflux overnight. The reaction mass is poured into warm, dilute soda solution with thorough stirring and filtered after cooling. 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, the p-amino-benzenesulfone-Nl- (a, a-dimethyl-a-benzyl-acetyl) -amide precipitating out. After reprecipitation from soda solution, the new compound can be obtained in pure form by recrystallization from dilute alcohol and then melts at 218.
The condensation of p-acetylamino-benzenesulfonamide with a, a-dimethyl-a-benzyl-acetic acid chloride can also be carried out in nitrobenzene with the addition of aluminum chloride or in pyridine instead of in chlorobenzene. A metal compound of p -Acetylamino-benzenesulfonamides run out and these react with a @, a-dimethyl-a-benzyl-acetic acid chloride.
Furthermore, you can p-acetylamino-benzenesulfonamide with a, a-dimethyl-a-benzyl-acetic acid in the presence of condensing agents, eg. B. of phosphorus pentoxide or of phosphorus pentachloride, implement.
The same end product is also obtained if a metal compound of a, a-dimethyl-a-benzyl-acetic acid amide is reacted with a p-acetylamino-benzenesulfohalide and the resulting acetyl compound is saponified.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH20T9520T | 1940-06-21 | ||
| CH253168T | 1943-09-14 | ||
| CH242285T | 1943-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253168A true CH253168A (en) | 1948-02-15 |
Family
ID=34139178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253168D CH253168A (en) | 1940-06-21 | 1943-09-14 | Process for the preparation of a p-amino-benzene-sulfonacylamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253168A (en) |
-
1943
- 1943-09-14 CH CH253168D patent/CH253168A/en unknown
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