CH191673A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-4-aminoanilide.Info
- Publication number
- CH191673A CH191673A CH191673DA CH191673A CH 191673 A CH191673 A CH 191673A CH 191673D A CH191673D A CH 191673DA CH 191673 A CH191673 A CH 191673A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanilide
- sulfanilic acid
- preparation
- acid
- sulfanilic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 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 compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
- 229950000244 sulfanilic acid Drugs 0.000 description 3
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- CHMBIJAOCISYEW-UHFFFAOYSA-N N-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OSZFJGLXXUAMEJ-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonyl chloride Chemical compound CC(=O)C1=CC(N)=CC=C1S(Cl)(=O)=O OSZFJGLXXUAMEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- -1 aromatic nitroamines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000706 filtrate 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 Sulfanilsäure-4-aminoanilid. Es wurde gefunden, dass Anilide der Sul- fanilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen Strepto- kokken aufweisen. Anilide der Sulfanilsäure aus aromatischen Diaminen waren bisher nicht bekannt.
Ihre Herstellung erfolgt durch Ein wirkung von Acylsulfanilsäurehalogeniden auf aromatische Diamine oder auf Monoäcylver- bindungen von aromatischen Diaminen und nachheriger Abspaltung der Acylgruppen oder durch Umsetzung von Acylsulfanilsäurehaloge- niden mit aromatischen Nitroaminen, Reduk tion und Abspaltung der 'Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-4-aminoanilid, welches dadurch gekenn zeichnet ist, dass man Acylsulfanilsäurehaloge- nid auf Monoacyl-p-phenylendiamin einwirken lässt und die Acylgruppen abspaltet.
Das Sulfanilsäure-4-aminoanilid schmilzt bei 138 . Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel:</I> <B>150</B> Teile Monoacetyl-p-phenylendiamin werden in 300 Teilen Methylalkohol mit der berechneten Menge von rohem, feuchtem Ace- tylsulfanilsäurechlorid unter Zusatz von Na tronlauge zur Reaktion gebracht. Dann gibt man 500 Teile Wasser und Natronlauge im Überschuss zu und filtriert das nicht umge setzte Monoacetyl-p-phenylendiamin ab. Das Filtrat wird angesäuert und das Kondensa tionsprodukt abgesaugt. Zur Abspaltung der Acetylgruppen wird es 1 Stunde mit 700 Tei len 15 o/oiger Salzsäure gekocht.
Die eDt- standene klare Lösung des Hydrochlorids wird neutralisiert und das Sulfanilsäure-4- aminoanilid unter Zusatz von Kohle aus Was ser umkristallisiert.
Process for the preparation of sulfanilic acid-4-aminoanilide. It has been found that anilides of sulphanilic acid from aromatic diamines have an excellent action against streptococci in vivo. Anilides of sulfanilic acid from aromatic diamines were not previously known.
They are produced by the action of acylsulfanilic acid halides on aromatic diamines or on monoacyl compounds of aromatic diamines and subsequent cleavage of the acyl groups or by reaction of acylsulfanilic acid halides with aromatic nitroamines, reduction and cleavage of the acyl group.
The subject of the present patent is a process for the preparation of sulfanilic acid-4-aminoanilide, which is characterized in that acylsulfanilic acid halide is allowed to act on monoacyl-p-phenylenediamine and the acyl groups are split off.
The sulfanilic acid 4-aminoanilide melts at 138. It is quite soluble in alcohol and methyl alcohol, and easily dissolves in acids and alkalis. The new compound is intended to be used as a medicine.
<I> Example: </I> <B> 150 </B> parts of monoacetyl-p-phenylenediamine are reacted in 300 parts of methyl alcohol with the calculated amount of crude, moist acetylsulfanilic acid chloride with the addition of sodium hydroxide solution. Then 500 parts of water and sodium hydroxide solution are added in excess and the unconverted monoacetyl-p-phenylenediamine is filtered off. The filtrate is acidified and the condensation product is filtered off with suction. To split off the acetyl groups, it is boiled with 700 parts of 15% hydrochloric acid for 1 hour.
The resulting clear solution of the hydrochloride is neutralized and the sulfanilic acid-4-aminoanilide is recrystallized from water with the addition of charcoal.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH191673A true CH191673A (en) | 1937-06-30 |
Family
ID=4437760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191673D CH191673A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH191673A (en) |
-
1936
- 1936-05-28 CH CH191673D patent/CH191673A/en unknown
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