CH302374A - Process for the preparation of a new acetoacetylamino compound. - Google Patents
Process for the preparation of a new acetoacetylamino compound.Info
- Publication number
- CH302374A CH302374A CH302374DA CH302374A CH 302374 A CH302374 A CH 302374A CH 302374D A CH302374D A CH 302374DA CH 302374 A CH302374 A CH 302374A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- new
- acetoacetylamino
- preparation
- acetic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- -1 acetoacetylamino compound Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer neuen Acetoacetylaminoverbindung. < egenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung einer neuen Acetoacetylaminov erbindung, nämlich des 1.-Acetoacetyla.mino-4-suIfonsäure-thiazo- lyl-(.?')-aniids, und, ist dadurch gekennzeich net, d'ass man 1-Amssno-4-s;
ttlfonsäure-.thiazolyl- (Z')-amiid in 90- bis 100prozentiger Essig säure bei einer Temperatur zwischen 40 und 80 C mit Diketen umsetzt.
Diese Verbindung ist .ein weisser, kristalli ner Körper vom Schmelzpunkt 184 bis 1.8'5o C, der in Wasser unlöslich, jedoch in Eisessig und Py ridin löslich ist.
Die so erhaltene Verbindung- lä.sst sieh mit den verschiedenartigsten Diazoverbindungen leielit kuppeln und ist somit ein wertvolles 'Lwisehenprodukt für die Herstellung von neuen Azofarbstoffen.
Die Umsetzung mit Diketen erfolgt vor <I>n</I> bei einer Temperatur von 60 bis <B>70"</B> C und in Gegenwart von Eisessig. <I>Beispiel:</I> 2>,5 Teile 1-Amino-4-sultonsäure-thiazolyl- (?')-amid werden in 150 Teilen Eisessig ge- löst und während 1 Stunde bei<B>65"</B> C 9,5 Teile Diketen unter Rühren zutropfen gelassen. Es wird noch 31/2 Stunden, bei dieser Tempera tur gerührt, erkalten gelassen und das kri stalline Reaktionsprodukt isoliert (Ausbeute 93 /o).
Process for the preparation of a new acetoacetylamino compound. The subject of the present invention is a process for the production of a new acetoacetylamine compound, namely the 1.-acetoacetyla.mino-4-sulfonic acid-thiazolyl - ( man 1-Amssno-4-s;
ttlfonsäure-.thiazolyl- (Z ') - amiid in 90--100 percent acetic acid at a temperature between 40 and 80 C with diketene.
This compound is a white, crystalline body with a melting point of 184 to 1.8'5o C, which is insoluble in water, but soluble in glacial acetic acid and pyridine.
The compound thus obtained can easily be coupled with the most varied of diazo compounds and is thus a valuable product for the production of new azo dyes.
The reaction with diketene takes place before <I> n </I> at a temperature of 60 to <B> 70 "</B> C and in the presence of glacial acetic acid. <I> Example: </I> 2>, 5 parts 1-Amino-4-sultonic acid-thiazolyl- (? ') - amide are dissolved in 150 parts of glacial acetic acid and 9.5 parts of diketene are added dropwise with stirring over 1 hour at 65 ° C. It is stirred for another 31/2 hours, at this tempera ture, allowed to cool and the crystalline reaction product is isolated (yield 93 / o).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH299706T | 1951-08-21 | ||
| CH302374T | 1951-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302374A true CH302374A (en) | 1954-10-15 |
Family
ID=25734089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302374D CH302374A (en) | 1951-08-21 | 1951-08-21 | Process for the preparation of a new acetoacetylamino compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302374A (en) |
-
1951
- 1951-08-21 CH CH302374D patent/CH302374A/en unknown
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