CH185341A - Process for the preparation of 2-acetoacetylamino-4-phenylthiazole. - Google Patents
Process for the preparation of 2-acetoacetylamino-4-phenylthiazole.Info
- Publication number
- CH185341A CH185341A CH185341DA CH185341A CH 185341 A CH185341 A CH 185341A CH 185341D A CH185341D A CH 185341DA CH 185341 A CH185341 A CH 185341A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenylthiazole
- acetoacetylamino
- preparation
- heated
- aminothiazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- ZOCHBPBYYHGZED-UHFFFAOYSA-N 3-oxo-n-(4-phenyl-1,3-thiazol-2-yl)butanamide Chemical compound S1C(NC(=O)CC(=O)C)=NC(C=2C=CC=CC=2)=C1 ZOCHBPBYYHGZED-UHFFFAOYSA-N 0.000 title description 3
- PYSJLPAOBIGQPK-UHFFFAOYSA-N 4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1 PYSJLPAOBIGQPK-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- HJZGXXPOKWGQHH-UHFFFAOYSA-N n-(4-phenyl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=CC=CC=2)=C1 HJZGXXPOKWGQHH-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 2-Acetoacetylamino-4-hhenylthiazol. Im Hauptpatent Nr. 171718 ist ein Ver fahren zur Herstellung von 2-Acylacetyl- amino-arylenthiazolen beschrieben. Es be steht darin, dass man 2-Aminoarylenthiazole mit Acylessigestern bis zur Bildung der ent sprechenden Arylide so lange auf höhere Temperaturen erhitzt, bis die Abspaltung des entsprechenden Alkohols beendet ist.
Es wurde nun gefunden, dass man an Stelle der im Hauptpatent genannten 2- Aminoarylenthiazole in gleicher Weise 2-Aminothiazole verwenden kann, die keine aaskondensierten Arylenreste enthalten. Sol che Verbindungen sind z. B. 2-Aminothiazol selbst und seine Kernsubstitutionsprodukte.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 2-Acetoacetylamino-4-phenylthiazol, welches dadurch gekennzeichnet ist, dass man 4-Phenyl-2-aminothiazol 'mit Acetessigsäure- äthylester auf höhere Temperaturen erhitzt. <I>Beispiel</I> <B>100</B> Gewichtsteile 4-Phenyl-2-aminotliia- zol (Ann. 249, S. 46, Fp. 184 ) werden mit 300 Gewichtsteilen Acetessigsäureäthylester aasgeschlämmt und unter Rühren etwa 15 Minuten auf 160 erhitzt.
Das 2-Aceto- acetylamino-4-phenylthiazol kristallisiert in farblosen Rhomben von Fp. 176 aus.
Process for the preparation of 2-acetoacetylamino-4-hhenylthiazole. In the main patent no. 171718 a process is described for the preparation of 2-acylacetylamino-arylenthiazoles. It is that 2-aminoarylenethiazoles with acyl acetic esters are heated to higher temperatures until the corresponding arylides are formed until the cleavage of the corresponding alcohol has ended.
It has now been found that, instead of the 2-aminoarylenothiazoles mentioned in the main patent, 2-aminothiazoles which contain no aas-condensed arylene radicals can be used in the same way. Such connections are z. B. 2-aminothiazole itself and its core substitution products.
The subject of the present patent is a process for the preparation of 2-acetoacetylamino-4-phenylthiazole, which is characterized in that 4-phenyl-2-aminothiazole is heated to higher temperatures with ethyl acetoacetate. <I> Example </I> <B> 100 </B> parts by weight of 4-phenyl-2-aminotliiazole (Ann. 249, p. 46, mp. 184) are slurried with 300 parts by weight of ethyl acetoacetate and about 15 parts by weight Heated to 160 minutes.
The 2-acetoacetylamino-4-phenylthiazole crystallizes out in colorless rhombuses with a melting point of 176.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE171718X | 1933-02-15 | ||
| US185341XA | 1933-09-02 | 1933-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185341A true CH185341A (en) | 1936-07-15 |
Family
ID=32963161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185341D CH185341A (en) | 1933-02-15 | 1934-02-06 | Process for the preparation of 2-acetoacetylamino-4-phenylthiazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185341A (en) |
-
1934
- 1934-02-06 CH CH185341D patent/CH185341A/en unknown
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