CH199682A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-4-aminoanilide.Info
- Publication number
- CH199682A CH199682A CH199682DA CH199682A CH 199682 A CH199682 A CH 199682A CH 199682D A CH199682D A CH 199682DA CH 199682 A CH199682 A CH 199682A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- aminoanilide
- preparation
- sulfanilic 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
- 239000002253 acid Substances 0.000 claims description 8
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- -1 acetylsulfanilic acid halides Chemical class 0.000 description 5
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229950000244 sulfanilic acid Drugs 0.000 description 3
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 2
- 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
- 238000009835 boiling Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VFAFNEXFRYYVSD-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1=C(S(=O)(=O)Cl)C=CC(=C1)N Chemical compound C(C1=CC=CC=C1)(=O)C1=C(S(=O)(=O)Cl)C=CC(=C1)N VFAFNEXFRYYVSD-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
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-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 Snlfanilsäure-4-aminoanilid. Es wurde gefunden, dass Anilide der Sulfanils:äure 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 Acetylsulfanil- säurehalogeniden auf aromatische Diamine oder auf Monoacetylverbindungen von aro matischen Diaminen und na;chheriger 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- säurehalogenid auf p-Nitranilin einwirken lässt und im so erhaltenen Produkt in be liebiger Reihenfolge die Nitrogruppe redu ziert und die Acylgruppe abspaltet.
Das \Sulfanilsäure-4-aminoanilid schmilzt bei<B>138'.</B> Es ist ziemlich löslich in Alkohol und iVIethylalkoh.ol und löst sich leicht in Säuren und Laugen. -Die neue Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel 1:</I> 35 Teile fast trockenes Propionylsulfanil- säurechlorid, 25 Teile p-Nitranilin und 1'5 Teile wasserfreies Natriumacetat werden gut gemischt und auf<B>20-30'</B> erhitzt. Nach dem Erkalten digeriert man die Masse mit 250 Teilen 10%iger Natronlauge und saugt das unveränderte, ungelöste p-Nitranilin ab.
Aus dem Filtrat fällt man das Propionylsulfanil- säure-4-nitroanilid durch Säurezusatz. Dieses wird in methylalkoholischer Suspension mit Wasserstoff bei Gegenwart eines Hydrie- rungskatalyGators behandelt. Man erhält das Propionylsulf anilsäure - 4 - aminoanilid, das man durch Kochen mit verdünnter Lauge oder Säure zum Sulfanilsäure-4-aminoanilid verseift.
Beispiel <I>2:</I> 35 Teile fast trockenes Benzoylsulfanil- säurechlorid, 20 Teile p-Nitranilin und 10 Teile wasserfreies Natriumacetat werden nach dem Mischen auf 110-130' erhitzt.
Nach Beendigung der Kondensation gibt man 250 Teile<B>10%</B> Natronlauge hinzu und kocht zwecks Abspaltung des Benzoylrestes 1-2 Stunden am Rückflusskühler. Dann lässt man erkalten und filtriert das unveränderte p-Nitranilin ab. Das Filtrat wird durch Säurezusatz neutralisiert.
Das rohe ,Sulfanil- säure-4-nitroanilid wird in alkalischer oder saurer Lösung durch Erwärmen mit Zink staub zum Sulfanilsäure-4-aminoanilid redu- ziert und verseift.
Process for the preparation of sulfanilic acid-4-aminoanilide. It has been found that anilides of sulfanilic acids from aromatic diamines have an excellent action against streptococci in vivo. Anilides of sulfanilic acid from aromatic diamines were not previously known.
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 halide is allowed to act on p-nitroaniline and the nitro group is reduced in any order in the product thus obtained and splitting off the acyl group.
The \ sulfanilic acid-4-aminoanilide melts at <B> 138 '. </B> It is quite soluble in alcohol and iVIethylalkoh.ol and easily dissolves in acids and alkalis. -The new compound is intended to be used as a medicine.
<I> Example 1: </I> 35 parts of almost dry propionylsulfanilic acid chloride, 25 parts of p-nitroaniline and 1'5 parts of anhydrous sodium acetate are mixed well and heated to <B> 20-30 '</B>. After cooling, the mass is digested with 250 parts of 10% sodium hydroxide solution and the unchanged, undissolved p-nitroaniline is filtered off with suction.
The propionylsulfanilic acid 4-nitroanilide is precipitated from the filtrate by adding acid. This is treated in a methyl alcoholic suspension with hydrogen in the presence of a hydrogenation catalyst. Propionylsulfanilic acid - 4 - aminoanilide is obtained, which is saponified by boiling with dilute lye or acid to form sulfanilic acid-4-aminoanilide.
Example <I> 2: </I> 35 parts of almost dry benzoylsulfanilic acid chloride, 20 parts of p-nitroaniline and 10 parts of anhydrous sodium acetate are heated to 110-130 'after mixing.
After the condensation has ended, 250 parts of 10% sodium hydroxide solution are added and the mixture is boiled in a reflux condenser for 1-2 hours in order to split off the benzoyl radical. It is then allowed to cool and the unchanged p-nitroaniline is filtered off. The filtrate is neutralized by adding acid.
The crude, sulfanilic acid 4-nitroanilide is reduced to sulfanilic acid 4-aminoanilide in an alkaline or acidic solution by heating with zinc dust and then saponified.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 | ||
| CH199682T | 1936-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199682A true CH199682A (en) | 1938-08-31 |
Family
ID=25722159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199682D CH199682A (en) | 1936-05-28 | 1936-11-05 | Process for the preparation of sulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199682A (en) |
-
1936
- 1936-11-05 CH CH199682D patent/CH199682A/en unknown
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