CH194682A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-4-aminoanilide.Info
- Publication number
- CH194682A CH194682A CH194682DA CH194682A CH 194682 A CH194682 A CH 194682A CH 194682D A CH194682D A CH 194682DA CH 194682 A CH194682 A CH 194682A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanilide
- acid
- preparation
- sulfanilic acid
- act
- 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
- 229950000244 sulfanilic acid Drugs 0.000 claims description 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 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 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
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 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
- 239000003638 reducing agent 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic nitroamines Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 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
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid 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 Sulfanilsäur e-4-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 Acylsulfanil- säurehalogeniden auf aromatische Diamine oder auf Monoacylverbindungen von aroma tischen Diaminen und nachherige Abspal tung der Acylgruppe oder durch Umsetzung von Acylsulfanilsäurehalogeniden mit aro matischen Nitroaminen, Reduktion und Ab spaltung der Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von,Sulfanil- säure-4-aminoanilid, welches dadurch ge kennzeichnet isst, dass man ein Aeylsulfanil- säurehalogenid auf p-Nitranilin einwirken lässt und das: so erhaltene Produkt, ein Re duktionsmittel und ein die Acylgruppe ab spaltendes Mittel aufeinander einwirken lässt.
Dae ;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> 60 Teile p-Nitranilin, 120 Teile rohes, getrocknetes Acetylsulfanilsäurechlorid und 60 Teile wasserfreies Natriumacetat werden auf 110 bis 120' erhitzt. Nach dem Erkal ten löst man die feste Masse in 10%iger Kalilauge.
Das nicht umgesetzte p-Nitranilin wird abfiltriert und kann nach dem Trock nen wieder verwendet werden. Die alkalische Lösung des. Kondensationsproduktes wird mit .Salze:äure neutralisiert. Das ausfallende, in Wasser unlösliche p-Acetylaminobenzol- sulfonyl-p-nitranilin wird abgesaugt und getrocknet.
Man löst es in der berechneten Menge verdünnter Natronlauge und hydriert unter Zusatz eines Nickelkatalysators bei 70 bis <B>90'</B> und 15 Atm. Nach Beendigung der Wasserstoffaufnahme filtriert man den Ka talysator ab und fällt das p-Acetylamino- benzolsulfonyl-p-phenylendiamin durch Zu satz von. verdünnter Essigsäure.
Zur Abspaltung der Acetylgruppe kocht man das Acetylamid i/2 Stunde mit 10 % iger Natronlauge und gewinnt so das @Sulfanil- säure-4-aminoanilid.
Process for the preparation of sulfanilic acid e-4-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 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-4-aminoanilide, which is characterized in that an Aeylsulfanilic acid halide is allowed to act on p-nitroaniline and the product thus obtained, a reducing agent and a die Lets acyl group from splitting agent act on each other.
Dae; 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> 60 parts of p-nitroaniline, 120 parts of crude, dried acetylsulfanilic acid chloride and 60 parts of anhydrous sodium acetate are heated to 110 to 120 °. After cooling, the solid mass is dissolved in 10% potassium hydroxide solution.
The unreacted p-nitroaniline is filtered off and can be used again after drying. The alkaline solution of the condensation product is neutralized with salts: acid. The p-acetylaminobenzenesulfonyl-p-nitroaniline which precipitates and is insoluble in water is filtered off with suction and dried.
It is dissolved in the calculated amount of dilute sodium hydroxide solution and hydrogenated with the addition of a nickel catalyst at 70 to 90 ° and 15 atm. After the uptake of hydrogen has ceased, the catalyst is filtered off and the p-acetylamino-benzenesulfonyl-p-phenylenediamine is precipitated by adding. dilute acetic acid.
To split off the acetyl group, the acetylamide is boiled for 1/2 hour with 10% sodium hydroxide solution and the @sulfanilic acid 4-aminoanilide is thus obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH194682T | 1936-05-28 | ||
| CH191673T | 1936-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194682A true CH194682A (en) | 1937-12-15 |
Family
ID=25722155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194682D CH194682A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194682A (en) |
-
1936
- 1936-05-28 CH CH194682D patent/CH194682A/en unknown
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