DE286093C - - Google Patents
Info
- Publication number
- DE286093C DE286093C DENDAT286093D DE286093DA DE286093C DE 286093 C DE286093 C DE 286093C DE NDAT286093 D DENDAT286093 D DE NDAT286093D DE 286093D A DE286093D A DE 286093DA DE 286093 C DE286093 C DE 286093C
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- oxazoles
- parts
- diaminoanthraquinone
- nitrobenzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- BSXBWLBCNVXEQB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-oxazole Chemical class C1=COC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BSXBWLBCNVXEQB-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- RZFVLEJOHSLEFR-UHFFFAOYSA-N phenanthridone Chemical class C1=CC=C2C(O)=NC3=CC=CC=C3C2=C1 RZFVLEJOHSLEFR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
- JVr 286093 -KLASSE 22 6. GRUPPE - JVR 286093 - CLASS 22 6. GROUP
Anthrachinonoxazole sind bereits in Anlehnung an die in der aromatischen Reihe üblichen Darstellungsverfahren aus o-Aminooxyanthrachinonen durch Erhitzen mit Säureanhydriden bzw. Säurechloriden (vgl. Ladeη-burg, Ber. 9, S. 1526, und P. Nawiasky, Zeitschrift für ang. Chemie 26, S. 438) oder mit Aldehyden (vgl. Patent 252839) erhalten worden.-Anthraquinone oxazoles are based on those customary in the aromatic series Preparation process from o-aminooxyanthraquinones by heating with acid anhydrides or acid chlorides (see Ladeη-burg, Ber. 9, p. 1526, and P. Nawiasky, Zeitschrift für ang. Chemie 26, p. 438) or with aldehydes (see patent 252839).
Als Anthrachinonoxazole wurden zudem durch P. Nawiasky (a. a. O.) und Fr. UIlmann und W. Junghanns (Ann. 399, S. 331 und 335) die zuerst für Phenanthridonderivate gehaltenen Produkte erkannt, die nach dem Patent 236857 durch Einwirkung von Benzoylchlorid bzw. Benzoesäureanhydrid auf o-Halogenaminoanthrachinone entstehen.As anthraquinone oxazoles, P. Nawiasky (op. Cit.) And Ms. UIlmann and W. Junghanns (Ann. 399, pp. 331 and 335) the first for phenanthridone derivatives Recognized products held according to patent 236857 through the action of benzoyl chloride or benzoic anhydride arise on o-haloaminoanthraquinones.
Es wurde nun gefunden, daß Anthrachinonoxazole direkt gewonnen werden, wenn man Acylaminoanthrachinone mit oxydierenden Mitteln behandelt.It has now been found that anthraquinone oxazoles are obtained directly if one Acylaminoanthraquinones treated with oxidizing agents.
C14H7O2-NHCOR-H2 = C14H6OC 14 H 7 O 2 -NHCOR-H 2 = C 14 H 6 O
i. 20 Teile Dibenzoyl-1 · 4 - diaminoanthrachinon werden in 150 Teilen Nitrobenzol suspendiert und dazu 15 Teile Salpetersäure vom spez. Gew. 1,52 unter allmählichem Erwärmen auf 50 ° zufließen lassen. Die Mischung wird dann noch einige Stunden unter Rühren auf etwa 950 erhitzt. Das Reaktionsprodukt wird abfiltriert, in etwa der 20 fachen Menge Nitrobenzol gelöst und etwa gebildetes Nitrodibenzoyl-i · 4-diaminoanthrachinon, das beim Erkalten kristallisiert, durch Filtration entfernt. Durch Konzentrieren der Laugen erhält man das 4 - Benzoylamino -1 · 2 -anthrachinon-jn-phenyloxazol in schönen orangefarbenen, bei 298 ° schmelzenden Nadeln.i. 20 parts of dibenzoyl-1 · 4 - diaminoanthraquinone are suspended in 150 parts of nitrobenzene and 15 parts of nitric acid of the spec. Wt. 1.52 allow to flow in with gradual heating to 50 °. The mixture is then heated for a few hours with stirring to about 95 0th The reaction product is filtered off, dissolved in about 20 times the amount of nitrobenzene and any nitrodibenzoyl-i · 4-diaminoanthraquinone formed, which crystallizes on cooling, is removed by filtration. By concentrating the alkaline solutions, 4-benzoylamino -1 · 2 -anthraquinone-jn-phenyloxazole is obtained in beautiful orange needles that melt at 298 °.
Der Körper ist ziemlich schwer in den gewöhnlichen Lösungsmitteln mit oranger Farbe löslich. Mit konzentrierter Schwefelsäure gibt er eine braunorange Lösung, die beim Er 2^ The body is rather difficult to dissolve in the common solvents of orange color. With concentrated sulfuric acid he gives a brown-orange solution, which in the case of Er 2 ^
hitzen fast farblos wird, indem die Benzoylgruppe abgespalten wird. Das so erhaltene Aminoderivat kristallisiert aus Nitrobenzol in dunkelvioletten, bei 360 ° schmelzenden Nadeln. heat becomes almost colorless as the benzoyl group is split off. The thus obtained Amino derivative crystallizes from nitrobenzene in dark purple needles that melt at 360 °.
2. 10 Teile Dibenzoyl-i · 4-diaminoanthrachinon werden mit der 20 fachen Menge Eisessig und etwa der gleichen Menge Bleisuperoxyd einige Stunden am Rückflußkühler erhitzt. Das Reaktionsprodukt wird dann abfiltriert und aus Chlorbenzol umkristallisiert. Das so erhaltene Öxazol besitzt die oben angegebenen Eigenschaften.2. 10 parts of dibenzoyl-i · 4-diaminoanthraquinone are made with 20 times the amount of glacial acetic acid and about the same amount of lead peroxide heated for a few hours on the reflux condenser. The reaction product is then filtered off and recrystallized from chlorobenzene. The oxazole thus obtained has those given above Properties.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE286093C true DE286093C (en) |
Family
ID=541441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT286093D Active DE286093C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE286093C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2090140A1 (en) * | 1970-05-19 | 1972-01-14 | Mitsui Toatsu Chemicals |
-
0
- DE DENDAT286093D patent/DE286093C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2090140A1 (en) * | 1970-05-19 | 1972-01-14 | Mitsui Toatsu Chemicals |
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