CH199684A - Process for the preparation of sulfanilic acid-3-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-3-aminoanilide.Info
- Publication number
- CH199684A CH199684A CH199684DA CH199684A CH 199684 A CH199684 A CH 199684A CH 199684D A CH199684D A CH 199684DA CH 199684 A CH199684 A CH 199684A
- 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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229950000244 sulfanilic acid Drugs 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000002252 acyl group Chemical group 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
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- -1 acetylsulphanilic acid halides Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- PEMGGJDINLGTON-UHFFFAOYSA-N N-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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 Sulfanilsäure 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 Aoetylsulfanil- sä.urehalogeniden auf aromatische Diamine oder auf Monoacetylverbindungen von aroma tischen Diaminen und naohheriger Abspal tung 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-3-aminoanilid, welches dadurch ge kennzeichnet ist, dass man ein Acylsulfanil- säurehalogenid auf ein Monoacyl-meta-phe- nylendiamin einwirken lässt und im so er haltenen Produkt die Acylgruppen ab spaltet.
Das Sulfanilsäure-3-aminoanilid schmilzt bei 158-160'. Es ist ziemlich löslich in Alkohol und. Methylalkohol und löst sieh leicht in Säuren und Laugen. Die neue Ver bindung soll als Arzneimittel verwendet werden. <I>Beispiel:</I> 30 Teile fast trockenes PropionyIsulfanil- säurechlorid werden mit 50' Teilen m-Amino- acetanilid durch gelindes Erwärmen in 1.00 Teilen Methylalkohol umgesetzt.
Das Kon densationsprodukt wird durch Kochen mit 150 Teilen 15%iger Salzsäure verseift. Man erhält das Sulfanilsäure-3-aminoanilid vom F. P.158-160 .
Process for the preparation of sulfanilic acid-3-aminoanilide. It has been found that anilides of sulfanilic 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 aoetylsulfanil acid halides on aromatic diamines or on monoacetyl compounds of aromatic diamines and closer elimination of the acetyl groups or by reaction of acetylsulphanilic acid halides with aromatic nitroamines, reduction and elimination of the acetyl groups.
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 monoacyl-meta-phenylenediamine and the acyl groups are removed in the product obtained in this way splits.
The sulfanilic acid 3-aminoanilide melts at 158-160 '. It is quite soluble in alcohol as well. Methyl alcohol and easily dissolves in acids and alkalis. The new connection is intended to be used as a drug. <I> Example: </I> 30 parts of almost dry propionyl isulphanilic acid chloride are reacted with 50 parts of m-aminoacetanilide in 1.00 parts of methyl alcohol by gentle heating.
The condensation product is saponified by boiling with 150 parts of 15% hydrochloric acid. The sulfanilic acid 3-aminoanilide of F.P. 158-160 is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 | ||
| CH199684T | 1936-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199684A true CH199684A (en) | 1938-08-31 |
Family
ID=25722161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199684D CH199684A (en) | 1936-05-28 | 1936-11-05 | Process for the preparation of sulfanilic acid-3-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199684A (en) |
-
1936
- 1936-11-05 CH CH199684D patent/CH199684A/en unknown
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