CH194683A - Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide.Info
- Publication number
- CH194683A CH194683A CH194683DA CH194683A CH 194683 A CH194683 A CH 194683A CH 194683D A CH194683D A CH 194683DA CH 194683 A CH194683 A CH 194683A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- sulfanilic acid
- aminoanilide
- preparation
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 title description 5
- 229950000244 sulfanilic acid Drugs 0.000 title description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000004820 halides 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
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- 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
- 150000003931 anilides Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical compound CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-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
- -1 aromatic nitroamines Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000020477 pH reduction Effects 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 Sulfanilsäure-2-methyl-6-aminoanilid. Es wurde gefunden, dass Anilide der Sulf- anilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen @Strepto- kokken aufweisen. Anilide der !Sulfanile.äure aus aromatischen Diaminen waren bisher nicht bekannt.
Ihre Herstellung erfolgt durch Einwirkung von Acylsulfanilsäurehalogeni- den auf aromatische Diamine oder auf Mono- acylverbindungen von aromatischen Diami nen und nachherige Abspaltung der Acyl- gruppe oder durch Umsetzung von Acylsulf- anilsäurehalogeniden mit aromatischen Ni- troaminen, Reduktion und Abspaltung der Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-2-methyl-5-aminoanilid, welches da durch gekennzeichnet ist, dass man ein Acyl- sulfanilsä,urehalogenid auf ein 1-Aminoh-2- m-ethyl@-,5-acylaminobenzdl einwirken lässt und im so erhaltenen Produkt die Acylgruppen abspaltet.
Das Sulfanilsäure-2-methyl-5-aminoanilid schmilzt bei 205 bis<B>206'.</B> Es ist ziemlich leicht löelich in Alkohol und Methylalkohol und löst sich leicht in ,Säuren und Laugen. Die neue Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel:</I> 2(h Teile 1-Amino-2-methyl-5-aoetylamino- benzol werden in 50 Teilen Methylalkohol mit der berechneten Menge von rohem, feuchtem Acetylsulfanilsäurechlorid unter Zusatz von verdünnter Natronlauge konden siert.
Die alkalische Lösung des Kondensa- tionsproduktes wird filtriert und das. Aeetyl- sulfanilsäure- 2 -,meth)rl-w,5!##acetylaminoanilid durch Ansäuern ausgefällt. Man verseift es durch Kochen mit 15%iger Salzsäure. Das entstehende Sulfanilsäure-2-methyl-5-amino- anilid wird aus, verdünntem Methylalkohol umkristallisiert.
Process for the preparation of sulfanilic acid 2-methyl-6-aminoanilide. It has been found that anilides of sulphanilic acid from aromatic diamines have an excellent effect 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 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-2-methyl-5-aminoanilide, which is characterized in that an acyl-sulfanilic acid, urehalide is added to a 1-aminoh-2- m-ethyl @ -, Lets 5-acylaminobenzdl act and splits off the acyl groups in the product thus obtained.
The sulfanilic acid-2-methyl-5-aminoanilide melts at 205 to <B> 206 '. </B> It is quite easily 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> 2 (h parts of 1-amino-2-methyl-5-aoetylamino-benzene are condensed in 50 parts of methyl alcohol with the calculated amount of crude, moist acetylsulfanilic acid chloride with the addition of dilute sodium hydroxide solution.
The alkaline solution of the condensation product is filtered and the acetylsulfanilic acid 2 -, meth) rl-w, 5! ## acetylaminoanilide is precipitated by acidification. It is saponified by boiling with 15% hydrochloric acid. The resulting sulfanilic acid 2-methyl-5-amino anilide is recrystallized from dilute methyl alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 | ||
| CH194683T | 1936-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194683A true CH194683A (en) | 1937-12-15 |
Family
ID=25722156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194683D CH194683A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194683A (en) |
-
1936
- 1936-05-28 CH CH194683D patent/CH194683A/en unknown
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