CH199683A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-4-aminoanilide.Info
- Publication number
- CH199683A CH199683A CH199683DA CH199683A CH 199683 A CH199683 A CH 199683A CH 199683D A CH199683D A CH 199683DA CH 199683 A CH199683 A CH 199683A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanilide
- acid
- preparation
- sulfanilic acid
- phenylenediamine
- 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 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- -1 acetylsulfanilic acid halides Chemical class 0.000 description 3
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- LWOAIKNLRVQTFT-UHFFFAOYSA-N 4-amino-N-(4-aminophenyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 LWOAIKNLRVQTFT-UHFFFAOYSA-N 0.000 description 1
- BWYAGJVIOZRNBM-UHFFFAOYSA-N C(CC)(=O)C1=C(S(=O)(=O)Cl)C=CC(=C1)N Chemical compound C(CC)(=O)C1=C(S(=O)(=O)Cl)C=CC(=C1)N BWYAGJVIOZRNBM-UHFFFAOYSA-N 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
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 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
- 238000003756 stirring Methods 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
Verfabren zur Darstellung von Sulfauilsäure-4-aminoanilid. Es wurde gefunden, dass Anilide der Sulfanilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung ,gegen Streptokokken aufweisen. Anilide der iSulf- anilsäure aus aromatischen Diaminen waren bisher nicht bekannt.
Ihre Herstellung er folgt -durch Einwirkung von Acetylsulfanil- säurehalogeniden auf aromatische Diamine oder auf Monoacetylverbin.dungen von aro matischen Diaminen und nachheriger Ab spaltung .der Acetylgruppen oder durch Um setzung von Acetylsulfanilsäurehalogeniden mit aromatischen Nitroaminen, Reduktion und Abspaltung der Acetylgruppen.
Gegenstand -des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-4-aminoanilid, welches dadurch ge kennzeichnet ist, dass man ein Acylsulfanil- säurehalogenicl auf p-Phenylendiamin ein wirken lässt und im so erhaltenen Produkt die Asylgruppe abspaltet.
Das Sulfanilsäure-4-aminoanilid schmilzt bei<B>138'.</B> 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> Zu<B>100</B> Teilen, in 200 Teilen Wasser ge löstem p-Phenylendiamin gibt man unter gutem Rühren langsam 40 Teile wenig feuchtes Propionylsulfanilsäureohlorid. Nach Beendigung der Umsetzung wird das rohe Kondensationsprodukt mit 15 % iger Salz säure :gekocht.
Nach dem Erkalten saugt man das in Salzsäure schwer lösliche Dihydrochlorid des Di-(p-amino-benzosulfo- nyl)-p-phenylendiamins ab und gewinnt das in Salzsäure sehr leicht lösliche Sulfanil- säure-4-aminoanilid durch Neutralisieren mit Alkalien.
Procedure for the preparation of sulfauilic 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 isulfanilic acid from aromatic diamines have not been known to date.
They are produced by the action of acetylsulfanilic acid halides on aromatic diamines or on monoacetyl compounds of aromatic diamines and subsequent cleavage of the acetyl groups or by reaction of acetylsulfanilic acid halides with aromatic nitroamines, reduction and cleavage of the acetyl groups.
The subject of the present patent is a process for the preparation of sulfanilic acid-4-aminoanilide, which is characterized in that an acylsulfanilic acid halogenicl is allowed to act on p-phenylenediamine and the asylum group is split off in the product thus obtained.
The sulfanilic acid-4-aminoanilide melts at <B> 138 '. </B> 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> To <B> 100 </B> parts of p-phenylenediamine dissolved in 200 parts of water, 40 parts of a little moist propionylsulfanilic acid chloride are slowly added with thorough stirring. After the reaction has ended, the crude condensation product is boiled with 15% hydrochloric acid.
After cooling, the dihydrochloride of di- (p-amino-benzosulphonyl) -p-phenylenediamine, which is sparingly soluble in hydrochloric acid, is suctioned off and the sulphanilic acid-4-aminoanilide, which is very easily soluble in hydrochloric acid, is obtained by neutralization with alkalis.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 | ||
| CH199683T | 1936-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199683A true CH199683A (en) | 1938-08-31 |
Family
ID=25722160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199683D CH199683A (en) | 1936-05-28 | 1936-11-05 | Process for the preparation of sulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199683A (en) |
-
1936
- 1936-11-05 CH CH199683D patent/CH199683A/en unknown
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