CH199685A - Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.Info
- Publication number
- CH199685A CH199685A CH199685DA CH199685A CH 199685 A CH199685 A CH 199685A CH 199685D A CH199685D A CH 199685DA CH 199685 A CH199685 A CH 199685A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- aminoanilide
- preparation
- methylsulfanilic
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- KXWAHIMRXJWIQM-UHFFFAOYSA-N NC1=CC=C(NS(=O)(C2=CC=C(C=C2)NC)=O)C=C1 Chemical compound NC1=CC=C(NS(=O)(C2=CC=C(C=C2)NC)=O)C=C1 KXWAHIMRXJWIQM-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- -1 aromatic nitroamines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- MSLICLMCQYQNPK-UHFFFAOYSA-N N-(4-bromophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Br)C=C1 MSLICLMCQYQNPK-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000047 product Substances 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
Description
Verfahren zur Darstellung von N-Nethylsulfanilsäure-4-aminoaniliä. Es wurde gefunden, dass Anilide der der Sulfanilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen Streptokokken aufweisen. Anilide der .Sulf- anilsäure aus aromatischen Aminen waren bisher nicht bekannt.
Ihre Darstellung kann dadurch erfolgen, dass man Acylsulfanil- säurehalogenide auf aromatische Diamine oder Monoacylverbindungen von aroma tischen Aminen einwirken lässt und die Asyl gruppen abspaltet oder Acylsulfanilsäure- halogenide mit aromatischen Nitroaminen umsetzt, reduziert und die Asylgruppen ab spaltet.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von N-Me- thylsulfanilsäure-4-aminoanilid, welches da durch gekennzeichnet ist, dass man ein N,N- Acylmethylsulfanilsäureamid mit einem Halogenacy lanilid mit Hilfe von Katalysa toren, wie Naturkupfer oder Kupferbronze, zum N,N'-Acyl-methylsulfanilsäure-4-acyl- aminoanilid umsetzt und die Asylgruppen abspaltet.
Das N-Methylsulfanilsäure-4-aminoanilid schmilzt bei 191-192'. Es ist unlöslich in kaltem und heissem Wasser, ziemlich löslich in Äthyl- und Methylalkohol, leicht löslich in Mineralsäuren und Alkalilaugen. Die neue Verbindung soll als Arzneimittel ver wendet werden.
<I>Beispiel:</I> 15 Teile N,N-Acetyl-methylsulfanilsäure- amid, 15 Teile p-Bromacetanilid, 10 Teile galiumkarbonat und 1/-9 Teil Naturkupfer C werden einige Zeit zum Schmelzen erhitzt. Die erkaltete Masse wird mit 200 Teilen 10%iger Natronlauge behandelt und das Alkaliunlösliche durch Filtrieren entfernt. Durch Neutralisieren gewinnt man das Kon densationsprodukt. Dieses wird durch Kochen mit 100 Teilen 10%iger Natronlauge ver seift.
Das N-Methylsulfanilsäure-4-amino- anilid wird am besten aus verdünntem Me thylalkohol umkristallisiert. PATENTANSPRUCH: Verfahren zur Darstellung von N.N-Me- thylsulfanilsäure-4-aminoanilid, dadurch ge kennzeichnet, daB man ein N,
N-Acylmethyl- sulfanilsäureamid mit einem Halogenacyl- anilid mit Hilfe eines Katalysators umsetzt und aus dem so erhaltenen Produkt die Acyl- ä ruppen abspaltet.
Das N-14lethylsulfanilsäure-4-aminoanilid schmilzt bei 191-192'. Es ist unlöslich in kaltem und heissem Wasser, ziemlich löslich in Äthyl- und Methylalkohol, leicht löslich in :Mineralsäuren und Alkalilaugen. Die neue Verbindung soll als Arzneimittel verwendet werden.
Process for the preparation of N-methylsulfanilic acid-4-aminoaniliä. It has been found that anilides of the sulfanilic acid from aromatic diamines have an excellent effect against streptococci in vivo. Anilides of .Sulfanilic acid from aromatic amines were not previously known.
They can be represented by letting acylsulfanilic acid halides act on aromatic diamines or monoacyl compounds of aromatic amines and splitting off the asylum groups or reacting acylsulphanilic acid halides with aromatic nitroamines, reducing them and splitting off the asylum groups.
The subject of the present patent is a process for the preparation of N-methylsulfanilic acid-4-aminoanilide, which is characterized by the fact that an N, N-acylmethylsulfanilic acid amide with a halogenacy lanilide with the help of catalysts, such as natural copper or copper bronze, is used for N, N'-acyl-methylsulfanilic acid-4-acyl-aminoanilide converts and splits off the asylum groups.
The N-methylsulfanilic acid-4-aminoanilide melts at 191-192 '. It is insoluble in cold and hot water, fairly soluble in ethyl and methyl alcohol, easily soluble in mineral acids and alkaline solutions. The new compound is intended to be used as a drug.
<I> Example: </I> 15 parts of N, N-acetylmethylsulfanilic acid amide, 15 parts of p-bromoacetanilide, 10 parts of galium carbonate and 1 / -9 part of natural copper C are heated for some time to melt. The cooled mass is treated with 200 parts of 10% sodium hydroxide solution and the alkali-insoluble material is removed by filtration. The condensation product is obtained by neutralization. This is soaped by boiling with 100 parts of 10% sodium hydroxide solution.
The N-methylsulfanilic acid-4-amino anilide is best recrystallized from dilute methyl alcohol. PATENT CLAIM: Process for the preparation of N.N-methylsulfanilic acid-4-aminoanilide, characterized in that an N,
N-acylmethylsulfanilic acid amide is reacted with a haloacyl anilide with the aid of a catalyst and the acyl groups are split off from the product thus obtained.
The N-14lethylsulfanilic acid 4-aminoanilide melts at 191-192 '. It is insoluble in cold and hot water, fairly soluble in ethyl and methyl alcohol, easily soluble in: mineral acids and alkaline solutions. The new compound is intended to be used as a medicine.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH194885T | 1937-01-11 | ||
| CH199685T | 1937-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199685A true CH199685A (en) | 1938-08-31 |
Family
ID=25722711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199685D CH199685A (en) | 1937-01-11 | 1937-01-11 | Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199685A (en) |
-
1937
- 1937-01-11 CH CH199685D patent/CH199685A/en unknown
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