AT69746B - Process for the preparation of sulfonic acids of aromatic aminothiazoles. - Google Patents
Process for the preparation of sulfonic acids of aromatic aminothiazoles.Info
- Publication number
- AT69746B AT69746B AT69746DA AT69746B AT 69746 B AT69746 B AT 69746B AT 69746D A AT69746D A AT 69746DA AT 69746 B AT69746 B AT 69746B
- Authority
- AT
- Austria
- Prior art keywords
- sulfonic acids
- aminothiazoles
- aromatic
- preparation
- dehydrothiotoluidine
- Prior art date
Links
- 150000003460 sulfonic acids Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- -1 aromatic aminothiazoles Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Sulfosäuren aromatischer Aminothiazole.
Bisiter sind nur solche Sulfosäuren des Dehydrothiotoluidins, seiner Homologen und Subatitutionsprodukte sowie der entsprechenden Primuline bekannt geworden, welche man durch Suincren der Basen mit rauchender Schwefelsäure gewinnt (siehe D. R. P. Nr. 51738, Nr. 47102 und Nr. 92011 u. a.).
Es wurde nun gefunden, dass man durch Erhitzen von Dehydrothiotoluidin mit Schwefelsäure auf höhere Temperaturen, den sogenannten Backprozess, zu einer Sulfosäure gelangt, die von der bisher bekannten Dehydrothiotoluidinsulfosäure wesentlich verschieden ist. Die neue Säure führt, diazotiert und mit Azokomponenten gekuppelt, zu Farbstoffen, die sich vor den
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durch Vertiefung der Nuance auszeichnen.
In derselben Weise lassen sich die Homologen des Dehydrothiotoluidius. wie das Dehvdro- thio-m-xylindin, seine Substitutionsprodukte, wie die durch Sulfieren des Dehydrothiotoh@idins mit rauchender Schwefelsäure darstellbare Sulfosäure sowie die entsprechenden Primuline in neue Sulfosäuren überführen, die sich von den bisher bekannten Sulfosäuren in ähnlicher Weise unterscheiden.
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Blättchen aus. Die Säure bildet eine intensiv gelb gefärbte, ziemlich schwerlösliche Diazoverbindung.
B e i s p i R l 2 : 268 Teile Dehydrothio-w.-xylidin werden mit einer Auflosung von 1U6 Teilen Schwefelsäuremonohydrat in Wasser innig vermischt und eingetrocknet. Das trockene Produkt erhitzt man dann mehrere Stunden im Vakuum am Rührwerk und absteigenden Kühler auf Temperaturen von 240 bis 270 im Ölbad. Wenn kein Wasser mehr überdestilliert, unterbricht
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ReaktionK rodukt alkalisch auf und fällt das Natronsatz der entstandenen Sulfo. säurc in der Wärme mit Kochsalz aus. Das gewonnene Produkt zieht fast farblos auf Baumwolle.
Die Anfärbung lässt t sich in üblicher Weise diazotieren und entwickeln.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of sulfonic acids of aromatic aminothiazoles.
Until now, only those sulfonic acids of dehydrothiotoluidine, its homologues and substitution products and the corresponding primulins have become known, which are obtained by suying the bases with fuming sulfuric acid (see D. R. P. No. 51738, No. 47102 and No. 92011 and others).
It has now been found that by heating dehydrothiotoluidine with sulfuric acid to higher temperatures, the so-called baking process, a sulfonic acid is obtained which is substantially different from the previously known dehydrothiotoluidine sulfonic acid. The new acid leads, diazotized and coupled with azo components, to dyes that are in front of the
EMI1.1
distinguished by deepening the nuance.
In the same way, the homologues of Dehydrothiotoluidius. such as dehydrothio-m-xylindine, its substitution products, such as the sulfonic acid which can be prepared by sulfating dehydrothiotohydin with fuming sulfuric acid, and the corresponding primulins, which differ from the previously known sulfonic acids in a similar way.
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Leaflets off. The acid forms an intensely yellow colored, rather poorly soluble diazo compound.
For example, 268 parts of dehydrothio-w.-xylidine are intimately mixed with a solution of 1U6 parts of sulfuric acid monohydrate in water and dried. The dry product is then heated for several hours in vacuo using the stirrer and descending cooler to temperatures of 240 to 270 in an oil bath. When no more water distills over, interrupt
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The reaction product becomes alkaline and the sodium substitute for the sulfo formed precipitates. acidic in the heat with table salt. The product obtained is almost colorless on cotton.
The staining can be diazotized and developed in the usual way.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69746X | 1913-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT69746B true AT69746B (en) | 1915-08-25 |
Family
ID=5635148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT69746D AT69746B (en) | 1913-06-23 | 1914-06-19 | Process for the preparation of sulfonic acids of aromatic aminothiazoles. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT69746B (en) |
-
1914
- 1914-06-19 AT AT69746D patent/AT69746B/en active
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