CH199686A - 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
- CH199686A CH199686A CH199686DA CH199686A CH 199686 A CH199686 A CH 199686A CH 199686D A CH199686D A CH 199686DA CH 199686 A CH199686 A CH 199686A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- aminoanilide
- catalyst
- preparation
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 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
- -1 aromatic nitroamines Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Nitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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-Rethylsulfanilsäure-4-aminoanilid. Es wurde gefunden, .dass Anilide 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 aromatischen Aminen einwirken lässt und .die Asylgruppen abspaltet oder Acylsulfanilsäurehalogenide mit aromatischen Nitroaminen umsetzt, redu ziert und die Asylgruppen abspaltet.
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- Acyl-methylsulfanilsäureamid mit p-Halogen- nitrobenzol mit Hilfe von Katalysatoren, wie Naturkupfer oder Kupferbronze, zum N,
N- Acyl-methylsulfanilsäure=4-nitroanilid um setzt und in beliebiger Reihenfolge die Nitro- gruppe reduziert und die Asylgruppe ab spaltet.
Das N-Methylsulfanilsäure-4-aminoanilid schmilzt bei 191-19,2'. Es ist unlöslich in kaltem und heissem Wasser, ziemlich löslich in Äthyl- und Methylalkohol, leicht löslieh in Mineralsäuren und Alkalilaugen. Die neue Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel:</I> 20 Teile N,N-Acetylmethylsulfani1säure- amid, 15 Teile p-Chlornitrobenzol, 10 Teile Kaliumkarbonat und 1 Teil Naturkupfer C werden auf etwa 200' erhitzt. Nach dem Erkalten digeriert man mit $00 Teilen 5%iger Kalilauge und filtriert.
Das Filtrat wird angesäuert und das ausfallende Kon- densationsprodukt mit 100 Teilen 10%iger Natronlauge gekocht. Beim Neutralisieren mit verdünnter Salzsäure fällt das N-Metlhyl- sulfanilsäure-4-nitroanilid aus.
Es wird aus Methylalkohol umkristallisiert und schmilzt bei<B>1810.</B> 10 Teile dieses Nitroanilids werden in 200 Teilen Methylalkohol unter Zusatz eines Nickelkatalysators bei<B>70--80'</B> mit Wasser stoff geschüttelt. Wenn die Wasserstoffauf- nahme beendigt ist, filtriert man den Kata lysator ab.
Nach dem Abdampfen des Me thylalkohols hinterbleibt das N-Methylsulf- anilsäure-4-aminoanilid.
Process for the preparation of N-Rethylsulfanilic acid-4-aminoanilide. It has been found that anilides of sulfanilic acid from aromatic diamines have an excellent effect in vivo against streptococci. 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 and reducing acylsulfanilic acid halides with aromatic nitroamines 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 that an N, N-acyl-methylsulfanilic acid amide with p-halo-nitrobenzene with the aid of catalysts such as Natural copper or copper bronze, for N,
N-acylmethylsulfanilic acid = 4-nitroanilide converts and in any order the nitro group is reduced and the asylum group is split off.
The N-methylsulfanilic acid-4-aminoanilide melts at 191-19.2 '. 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.
<I> Example: </I> 20 parts of N, N-acetylmethylsulfaniic acid amide, 15 parts of p-chloronitrobenzene, 10 parts of potassium carbonate and 1 part of natural copper C are heated to about 200 '. After cooling, it is digested with $ 00 parts of 5% potassium hydroxide solution and filtered.
The filtrate is acidified and the condensation product which precipitates is boiled with 100 parts of 10% strength sodium hydroxide solution. When neutralizing with dilute hydrochloric acid, the N-methylsulfanilic acid 4-nitroanilide precipitates.
It is recrystallized from methyl alcohol and melts at <B> 1810. </B> 10 parts of this nitroanilide are shaken with hydrogen in 200 parts of methyl alcohol with the addition of a nickel catalyst at <B> 70-80 '</B>. When the uptake of hydrogen has ceased, the catalyst is filtered off.
After the methyl alcohol has evaporated, the N-methylsulfanilic acid 4-aminoanilide remains.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH194885T | 1937-01-11 | ||
| CH199686T | 1937-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199686A true CH199686A (en) | 1938-08-31 |
Family
ID=25722712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199686D CH199686A (en) | 1937-01-11 | 1937-01-11 | Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199686A (en) |
-
1937
- 1937-01-11 CH CH199686D patent/CH199686A/en unknown
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