CH302373A - Process for the preparation of a new acetoacetylamino compound. - Google Patents
Process for the preparation of a new acetoacetylamino compound.Info
- Publication number
- CH302373A CH302373A CH302373DA CH302373A CH 302373 A CH302373 A CH 302373A CH 302373D A CH302373D A CH 302373DA CH 302373 A CH302373 A CH 302373A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- new
- acetoacetylamino
- acetic acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- -1 acetoacetylamino compound Chemical class 0.000 title description 4
- 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000725 suspension Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Herstellung einer neuen Acetoacetylaminoverbindung. Gegenstand der vorliegenden Erfindung ist ein Verfahren: zur Herstellung einer neuen:
Acetoacetylaminoverbindung, nämlich des Acetoacetylearbazols, und ist dadurch ge- kennzeichnet, dass man Carbazol in 90- bis 100prozentiger Essigsäure bei einer Tempera tur zwischen 40 und 80 C mit Diketen um- setzt.
Diese Verbindung ist ein weisser, kristalli ner Körper vom Schmelzpunkt 118 bis 120 C, der in Wasser unlöslich, jedoch in Eisessig, Alkohol und Benzol löslich ist.
Die so erhaltene Verbindung lässt sich mit den verschiedenartigsten Dia-zoverbindungen leicht kuppeln und ist somit ein wertvolles Zwischenprodukt für die Herstellung von neuen Azofarbstoffen.
Die Umsetzung mit Diketen, erfolgt vor- zugsweise bei einer Temperatur von 60 his 70 C unfl in Gegenwart von Eisessig.
<I>Beispiel:</I> <B>85</B> Teile Carbazol werden in 600 Teilen Eisessig suspendiert. In die Suspension wer den im Verlaufe von 51/z Stunden bei 6-5 %; 85 'Teile Diketen zutropfen gelassen, wobei die suspendierte Verbindung langsam in Lösung geht.
Es wird, dann noch während 3i/2 Stun den bei dieser Temperatur weiter. gerührt, worauf das Reaktionsgemisch erkalten gelas sen. und das kristalline Reaktionsprodukt isoliert wird (Ausbeute 80%).
Process for the preparation of a new acetoacetylamino compound. The present invention relates to a method: for producing a new:
Acetoacetylamino compound, namely acetoacetylearbazole, and is characterized in that carbazole is reacted with diketene in 90 to 100 percent acetic acid at a temperature between 40 and 80 C.
This compound is a white, crystalline body with a melting point of 118 to 120 C, which is insoluble in water, but soluble in glacial acetic acid, alcohol and benzene.
The compound obtained in this way can easily be coupled with a wide variety of diazo compounds and is thus a valuable intermediate for the production of new azo dyes.
The reaction with diketene is preferably carried out at a temperature of 60 to 70 C unfl in the presence of glacial acetic acid.
<I> Example: </I> <B> 85 </B> parts of carbazole are suspended in 600 parts of glacial acetic acid. In the suspension who the in the course of 51 / z hours at 6-5%; 85 parts of diketene are added dropwise, the suspended compound slowly dissolving.
It will then continue at this temperature for 3½ hours. stirred, whereupon the reaction mixture let cool down. and the crystalline reaction product is isolated (yield 80%).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH302373T | 1951-08-21 | ||
| CH299706T | 1951-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302373A true CH302373A (en) | 1954-10-15 |
Family
ID=25734088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302373D CH302373A (en) | 1951-08-21 | 1951-08-21 | Process for the preparation of a new acetoacetylamino compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302373A (en) |
-
1951
- 1951-08-21 CH CH302373D patent/CH302373A/en unknown
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