CH194684A - Process for the preparation of sulfanilic acid-3-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-3-aminoanilide.Info
- Publication number
- CH194684A CH194684A CH194684DA CH194684A CH 194684 A CH194684 A CH 194684A CH 194684D A CH194684D A CH 194684DA CH 194684 A CH194684 A CH 194684A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanilide
- acid
- preparation
- sulfanilic acid
- acyl
- 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 7
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- 229950000244 sulfanilic acid Drugs 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drugs Drugs 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
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- -1 aromatic nitroamines Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- NALDFXSDXQXFPL-UHFFFAOYSA-N (3-acetamidophenyl)azanium;chloride Chemical compound [Cl-].CC(=O)NC1=CC=CC([NH3+])=C1 NALDFXSDXQXFPL-UHFFFAOYSA-N 0.000 description 1
- 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
- VEXDRERIMPLZLU-UHFFFAOYSA-N 3-hydroxy-2-methylbutanoic acid Chemical compound CC(O)C(C)C(O)=O VEXDRERIMPLZLU-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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-3-aminoanilid. Es wurde gefunden, dass Anilide -der Sulf- a.nilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen Streptokokken aufweisen. Anilide der Sulf- anilsäure aus, aromatischen Diaminen waren bisher nicht bekannt.
Ihre Herstellung er folgt durch Einwirkung von Acylsulfanil- säurehalogeni4en auf aromatische Diamine oder auf Monoacylverbindungen von aroma tischen Diaminen und nachherige Abspal tung der Acylgruppe oder durch Umsetzung von Acylsulfanileäurehalogeniden mit aro matischen Nitroaminen, Reduktion und Ab spaltung der Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-3-aminoanilid, welches dadurch ge kennzeichnet ist, :dass man ein Acylsulfanil- säurehalogenid auf ein Mono-acyl-meta-phe- nylendiamin einwirken lässt und im so er haltenen Produkt .die Acylgruppen abspaltet.
Das Sulfanilsäure-.3-aminoanilid schmilzt bei 158 bis<B>160'.</B> Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Ver bindung soll als Arzneimittel verwendet werden.
<I>Beispiel;</I> 40 Teile Monoacetyl-m-phenylendiamin- hydrochlorid werden in wässeriger Lösung mit @d-er berechneten Menge von rohem, feuchtem Acetylsulfanilsäurechlorid versetzt. Durch langsamen Zusatz von verdünnter Natronlauge wird die Kondensation bewirkt. Die alkalische Lösung wird filtriert und das Kondensationsprodukt @dureh Säurezusatz ausgefällt.
Das Acetylsulfanilsäure-3-acetyl- aminoanilid wird zur Abspaltung .der Ace- tylgruppen mit 2.50 Teilen 15 % iger Salz säure gekocht. Die Lösung des, Hydrochlo- rids wird neutralisiert, das auskristallisie rende Sulfanilsäure-3-aminoanilid abgesaugt und auG Wasser umkristallisiert.
Process for the preparation of sulfanilic acid-3-aminoanilide. It has been found that anilides -der sulf-a.nilic acid from aromatic diamines have an excellent action against streptococci in vivo. Anilides of sulphanilic 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 group 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-3-aminoanilide, which is characterized in that: an acylsulfanilic acid halide is allowed to act on a mono-acyl-meta-phenylenediamine and in the product obtained in this way . splits off the acyl groups.
The sulfanilic acid .3-aminoanilide melts at 158 to <B> 160 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new connection is intended to be used as a drug.
<I> Example; </I> 40 parts of monoacetyl-m-phenylenediamine hydrochloride are mixed with the calculated amount of crude, moist acetylsulfanilic acid chloride in aqueous solution. The condensation is caused by the slow addition of dilute sodium hydroxide solution. The alkaline solution is filtered and the condensation product is precipitated from the addition of acid.
The acetylsulfanilic acid 3-acetylaminoanilide is boiled with 2.50 parts of 15% hydrochloric acid to split off the acetyl groups. The solution of the hydrochloride is neutralized, the sulfanilic acid 3-aminoanilide which crystallizes out is filtered off with suction and recrystallized from water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 | ||
| CH194684T | 1936-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194684A true CH194684A (en) | 1937-12-15 |
Family
ID=25722157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194684D CH194684A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid-3-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194684A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001002350A2 (en) * | 1999-06-30 | 2001-01-11 | Bayer Aktiengesellschaft | Novel amino sulfonamides and amido sulfonamides as antiviral agents |
-
1936
- 1936-05-28 CH CH194684D patent/CH194684A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001002350A2 (en) * | 1999-06-30 | 2001-01-11 | Bayer Aktiengesellschaft | Novel amino sulfonamides and amido sulfonamides as antiviral agents |
| WO2001002350A3 (en) * | 1999-06-30 | 2001-03-29 | Bayer Ag | Novel amino sulfonamides and amido sulfonamides as antiviral agents |
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