CH120429A - Process for the preparation of a new sulfur- and nitrogen-containing condensation product from the action product of chlorosulfur on p-anisidine. - Google Patents
Process for the preparation of a new sulfur- and nitrogen-containing condensation product from the action product of chlorosulfur on p-anisidine.Info
- Publication number
- CH120429A CH120429A CH120429DA CH120429A CH 120429 A CH120429 A CH 120429A CH 120429D A CH120429D A CH 120429DA CH 120429 A CH120429 A CH 120429A
- Authority
- CH
- Switzerland
- Prior art keywords
- product
- anisidine
- new
- nitrogen
- preparation
- Prior art date
Links
- 239000000047 product Substances 0.000 title claims description 6
- NGDNCZPCIZNCQS-UHFFFAOYSA-N ctk3j8699 Chemical compound Cl=S NGDNCZPCIZNCQS-UHFFFAOYSA-N 0.000 title claims description 5
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 title claims description 3
- 239000007859 condensation product Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 title description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229940122930 Alkalising agent Drugs 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- WJNRRJVYIOBHJF-UHFFFAOYSA-N 2-amino-5-anilinobenzenethiol Chemical compound C1=C(S)C(N)=CC=C1NC1=CC=CC=C1 WJNRRJVYIOBHJF-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines neuen schwefel- und stickstoffhaltigen Ifondensations- produktes aus dem Einwirkungsprodukt von Chlorschwefel auf p-Anisiclin: Wird das Einwirkungsprodukt von Chlor schwefel auf p-Anisidin von wahrscheinlich folgender Konstitution:
EMI0001.0008
mit Anilin. kondensiert, so entsteht unter Austausch der Oxyalkylgruppe gegen den I'henylaminorest eine neue Verbindung mit ganz ähnlichen Eigenschaften wie die im Hauptpatent beschriebene; sie besitzt wahr scheinlich folgende Zusammensetzung:
EMI0001.0011
Die neue Verbindung soll zur Herstel lung von Farbstoffen und pharmazeutischen Produkten benutzt werden. <I>Beispiel:</I> 22 kg des fein gemahlenen Einwirkungs produktes von Chlorschwefel auf p-Anisidin (siehe D. R. P. Nr. 360690, Beispiel 6, 2. Ab satz) werden bei gewöhnlicher Temperatur in eine Lösung von 10 kg Anilin in etwa 30 kg Eisessig eingetragen und mehrere Stunden gerührt. Die Reaktion verläuft un ter starker Wärmeentwicklung. Sobald, die Ausscheidung des Kondensationsproduktes nicht mehr zunimmt, giesst man das Reak tionsgemisch in mit Salzsäure angesäuertes Salzwasser von etwa 15 B6 und filtriert den kristallinischen Niederschlag ab.
Zur Reinigung kristallisiert man ihn aus stark verdünnter Salzsäure oder Essigsäure um.
Man erhält dann metallglänzende Nadeln oder Blättchen, welche sich mit kräftig rot violetter Farbe in Wasser lösen und auf tan nierte Baumwolle mit gleicher Farbe auf ziehen. Alkalien bezw. Alkalien und Re duktionsmittel spalten die neue Verbindung in 5-Phenylamino-2-amino-l-merkaptobenzol von der Formel:
EMI0002.0001
Process for the preparation of a new sulfur- and nitrogen-containing ifondensation product from the action product of chlorosulphur on p-anisicline: If the action product of chlorosulphur on p-anisidine will probably have the following constitution:
EMI0001.0008
with aniline. condensed, a new compound with properties very similar to those described in the main patent is formed by replacing the oxyalkyl group with the phenylamino radical; it probably has the following composition:
EMI0001.0011
The new compound is to be used in the manufacture of dyes and pharmaceutical products. <I> Example: </I> 22 kg of the finely ground action product of chlorosulphur on p-anisidine (see DRP no. 360690, example 6, 2nd paragraph) are at normal temperature in a solution of 10 kg aniline in about Entered 30 kg of glacial acetic acid and stirred for several hours. The reaction takes place under intense heat development. As soon as the excretion of the condensation product no longer increases, the reaction mixture is poured into salt water acidified with hydrochloric acid of about 15 B6 and the crystalline precipitate is filtered off.
To clean it, it is recrystallized from very dilute hydrochloric acid or acetic acid.
This gives shiny metal needles or flakes, which dissolve in water with a strong red-violet color and pull on tan-ned cotton with the same color. Alkalis respectively Alkalis and reducing agents split the new compound into 5-phenylamino-2-amino-1-mercaptobenzene of the formula:
EMI0002.0001
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH120429T | 1925-08-04 | ||
| CH117993T | 1925-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH120429A true CH120429A (en) | 1927-05-16 |
Family
ID=25708925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH120429D CH120429A (en) | 1925-08-04 | 1925-08-04 | Process for the preparation of a new sulfur- and nitrogen-containing condensation product from the action product of chlorosulfur on p-anisidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH120429A (en) |
-
1925
- 1925-08-04 CH CH120429D patent/CH120429A/en unknown
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