DE286094C - - Google Patents
Info
- Publication number
- DE286094C DE286094C DENDAT286094D DE286094DA DE286094C DE 286094 C DE286094 C DE 286094C DE NDAT286094 D DENDAT286094 D DE NDAT286094D DE 286094D A DE286094D A DE 286094DA DE 286094 C DE286094 C DE 286094C
- Authority
- DE
- Germany
- Prior art keywords
- derivatives
- anthraquinone
- benzoylamino
- oxazoles
- nitro
- 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
- 238000000034 method Methods 0.000 claims description 3
- 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 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002916 oxazoles Chemical class 0.000 description 2
- RZFVLEJOHSLEFR-UHFFFAOYSA-N phenanthridone Chemical class C1=CC=C2C(O)=NC3=CC=CC=C3C2=C1 RZFVLEJOHSLEFR-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- LWJALGMORUVODQ-UHFFFAOYSA-N N-benzoyl-N-(9,10-dioxoanthracen-1-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)N(C=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C=CC=1)C(=O)C1=CC=CC=C1 LWJALGMORUVODQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVr 286094 -KLASSE 226. GRUPPE- JVr 286094 - CLASS 226th GROUP
Verfahren zur Darstellung von Anthrachinonoxazolen. Patentiert im Deutschen Reiche vom 28. Oktober 1913 ab. Process for the preparation of anthraquinone oxazoles. Patented in the German Empire on October 28, 1913.
In der Patentschrift 236857, Kl. 22 b, ist angegeben, daß beim Erhitzen von Benzoylamino-o-halogenanthrachinonen mit kondensierenden Mitteln Phenanthridonderivate entstehen, indem eine Halogenwasserstoffabspaltung zwischen dem Halogen des Anthrachinonrestes und einem orthoständigen Η-Atom der Benzoylgruppe stattfindet. Diese angeblichen Phenanthridonderivate wurden durch die Untersuchungen von P. Nawiasky (Zeitschrift für ang. Chemie 26, Seite 438) und von Fr. Ulimann und W. Junghanns (Ann. 399, Seite 331 und 335) als Anthrachinon-pphenyloxazole charakterisiert.In the patent specification 236857, class 22 b, it is indicated that when heating benzoylamino-o-halogenanthraquinones with condensing agents phenanthridone derivatives are formed by splitting off hydrogen halide between the halogen of the anthraquinone residue and an ortho Η atom of the Benzoyl group takes place. These alleged phenanthridone derivatives were identified by the investigations by P. Nawiasky (Zeitschrift für ang. Chemie 26, page 438) and by Fr. Ulimann and W. Junghanns (Ann. 399, pages 331 and 335) as anthraquinone-pphenyloxazole characterized.
Es wurde nun gefunden, daß eine innere Kondensation ebenfalls stattfindet, wenn man Benzoylamino-o-nitroanthrachinone mit kondensierenden Mitteln behandelt, und daß auch die so erhältlichen Derivate Oxazole sind.It has now been found that internal condensation also takes place when one Benzoylamino-o-nitroanthraquinones treated with condensing agents, and that too the derivatives obtainable in this way are oxazoles.
H6 O2 <H 6 O 2 <
,NHCOC6H5 , NHCOC 6 H 5
— N- N
-NO9 -NO 9
O2H = C14 H6 O2 <O 2 H = C 14 H 6 O 2 <
CSH,C S H,
Die Verwendbarkeit der Benzoylamino-onitroänthrachinone zu diesem Zweck ist durchaus überraschend, da Halogen- und Nitroderivate auch in der Anthrachinonreihe in ihren Reaktionen nicht allgemein übereinstimmen und insbesondere Anthrachinonderivate, die eine Nitrogruppe in 2-Stellung enthalten, sonst recht beständig sind. Somit war eine glatte Bildung von Oxazolen unter Abspaltung von salpetriger Säure beim vorliegenden Verfahren nicht von vornherein zu erwarten.The usability of the benzoylamino-onitroanthraquinones for this purpose it is quite surprising that halogen and nitro derivatives are also in their anthraquinone series Reactions do not generally match, and in particular anthraquinone derivatives that contain a nitro group in the 2-position, are otherwise quite stable. Thus it was a smooth one Formation of oxazoles with elimination of nitrous acid in the present process not to be expected in advance.
' 2 Teile des in der Patentschrift 254185 beschriebenen 2-Nitro-i · 4-dibenzoylaminoanthrachinons werden mit 2 Teilen calc. Soda und 10 Teilen Naphtalin etwa 1 Stunde am Rückflußkühler erhitzt. Das nach dem Entfernen des Naphtalins mittels Alkohols und dem Auswaschen mit Wasser erhaltene Reaktionsprodukt ist reines 4-Benzoylamino-i · 2-anthrachinonju-pheriyloxazol. '2 parts of that described in patent specification 254185 2-Nitro-i · 4-dibenzoylaminoanthraquinones are calc with 2 parts. Soda and 10 parts of naphthalene refluxed for about 1 hour. That after removal of the naphthalene obtained by means of alcohol and washing with water is pure 4-benzoylamino-i · 2-anthraquinoneju-pheriyloxazole.
Aus Chlorbenzol kristallisiert es in schönen orangefarbenen, bei 298 ° schmelzenden Nadeln. Der Körper ist ziemlich schwer in den gewöhnlichen Lösungsmitteln mit oranger Farbe löslich. Mit konzentrierter Schwefelsäure gibt er eine braunorange Lösung, die beim Erhitzen fast farblos wird, indem die Benzoylgruppe abgespalten wird. Das so erhaltene Aminoderivat kristallisiert aus Nitrobenzol in dunkelvioletten, bei 360 ° schmelzenden Nadeln.It crystallizes from chlorobenzene in beautiful orange needles that melt at 298 °. The body is quite heavy in the common solvents with an orange color soluble. With concentrated sulfuric acid he gives a brown-orange solution, which when heated 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 °.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE286094C true DE286094C (en) |
Family
ID=541442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT286094D Active DE286094C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE286094C (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 DENDAT286094D patent/DE286094C/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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