DE252642C - - Google Patents
Info
- Publication number
- DE252642C DE252642C DENDAT252642D DE252642DA DE252642C DE 252642 C DE252642 C DE 252642C DE NDAT252642 D DENDAT252642 D DE NDAT252642D DE 252642D A DE252642D A DE 252642DA DE 252642 C DE252642 C DE 252642C
- Authority
- DE
- Germany
- Prior art keywords
- dinitro
- chlorobenzene
- carbazole
- leucoindophenol
- heated
- 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- YRUPBAWWCPVHFT-UHFFFAOYSA-N 4-(4-hydroxyanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C(O)C=C1 YRUPBAWWCPVHFT-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical class OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9H-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- 241000698776 Duma Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001021 Polysulfide Polymers 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Classifications
-
- 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
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
•KAISERLICHES• IMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVf 252642 KLASSE \2p. GRUPPE- JVf 252642 CLASS \ 2p. GROUP
Patentiert im Deutschen Reiche vom 23. Juli 1911 ab.Patented in the German Empire on July 23, 1911.
Durch Einwirkung von 2 · 4-Dinitro-i-chlorbenzol auf diej enigen Leukoindophenole, welche aus Carbazol, dessen am Stickstoff oder im Kern substituierten Derivaten einerseits und p-Nitrosophenolen andererseits in Gegenwart von Alkalien entstehen, werden neue wohlcharakterisierte Körper erhalten, deren technische Verwendbarkeit insbesondere darin beBy the action of 2 · 4-dinitro-i-chlorobenzene on those leucoindophenols which are derived from carbazole, its nitrogen or im Nuclear substituted derivatives on the one hand and p-nitrosophenols on the other hand in the presence arise from alkalis, new, well-characterized bodies are obtained, their technical Usability in particular be
steht, daß sie beim Erhitzen mit Polysulfiden in wertvolle Farbstoffe übergeführt werden können. : it says that they can be converted into valuable dyes when heated with polysulfides. :
Vermutlich erfolgt der Eingriff des 2 · 4-Dinitro-i-chlorbenzols in die Hydroxylgruppe des Leukoindophenols, und die neuen Körper besitzen folgende allgemeine Konstitutionsformel : Presumably the intervention of the 2 · 4-dinitro-i-chlorobenzene takes place into the hydroxyl group of leucoindophenol, and the new bodies have the following general constitutional formula:
NHNH
H (bzw. Alkyl) H (or alkyl)
Stickstoffbestimmungen nach Dumas von den Kondensationsprodukten aus Dinitrochlorbenzol undNitrogen determinations according to Dumas of the condensation products from dinitrochlorobenzene and
a) dem Leukoindophenol aus Carbazol und p-Nitrosophenol,a) the leucoindophenol from carbazole and p-nitrosophenol,
b) dem Leukoindophenol aus N - Äthylcarbazol und ρ - Nitrosophenolb) the leucoindophenol from N - ethyl carbazole and ρ - nitrosophenol
gaben für obige Formel gut stimmende Werte.gave well-fitting values for the above formula.
a) 0,2106 g Substanz gaben bei 130C. und 713 mm Barometerstand 25 ecm N; d. i. gefunden 13,12 Proz. N, berechnet 12,73 Proz. N. a) 0.2106 g gave substance at 13 0 C. and 713 mm barometer 25 ecm N; di found 13.12 percent N, calculated 12.73 percent N.
b) 0,1686 g Substanz gaben bei 130C. und 713 mm Barometerstand 17,8 ecm IV; d.i. gefunden 11,67 Pro2· N, berechnet 11,97 Proz. IV.b) 0.1686 g gave substance at 13 0 C. and 713 mm barometer 17.8 cc IV; di found 11.67 per 2 · N, calculated 11.97 per cent IV.
27 Teile der Leukoverbindung des aus Carbazol und p-Nitrosophenol erhältlichen Indo-27 parts of the leuco compound of the indo-
NO,NO,
NO2.NO 2 .
phenols werden in der zehnfachen Menge Alkohol gelöst und mit einer Lösung von ι Äquivalent Ätzkali versetzt. Hierzu fügt man nach und nach eine alkoholische Lösung von ι Mol. 2 · 4-Dinitro-i-chlorbenzol und erhitzt mehrere Stunden am Rückflußkühler. Das auskristallisierte Kondensationsprodukt wird abgesaugt; man erhält so in vorzüglicher Ausbeute ein reines Produkt vom Fp. 190°. Der Körper ist schwer löslich in Alkohol, Eisessig, Benzin, Chloroform, etwas leichter in Aceton. Beim Erwärmen löst er sich leicht in Anilin und Nitrobenzol; aus diesen Lösungsmitteln kristallisiert er in glänzenden kupferfarbenen Blättchen.phenols are dissolved in ten times the amount of alcohol and with a solution of ι equivalent of caustic potash added. To this end, an alcoholic solution is gradually added of ι Mol. 2 · 4-Dinitro-i-chlorobenzene and heated several hours on the reflux condenser. The condensation product which has crystallized out is filtered off with suction; one receives so in excellent Yield of a pure product with a melting point of 190 °. The body is sparingly soluble in alcohol, Glacial acetic acid, gasoline, chloroform, a little lighter in acetone. It dissolves when heated easily converts to aniline and nitrobenzene; from these solvents it crystallizes in glossy ones copper-colored leaves.
In analoger Weise werden Kondensationsprodukte aus den Indophenolen erhalten, die sich von den am Stickstoff substituierten Car-In an analogous manner, condensation products are obtained from the indophenols which differ from the car-
bazolen ableiten. Das Kondensationsprodukt aus 2 · 4-Dinitro-i-chlorbenzol und dem Leukoindophenol aus iV-Äthylcarbazol und p-Nitrosophenol ist von rotbrauner Farbe und kristallisiert in kleinen Nadeln. Der Schmelzpunkt liegt bei 223 °. Es ist sehr schwer löslich in Alkohol, Eisessig, Benzin, Chloroform und Tetrachlorkohlenstoff, etwas leichter in Benzol, leicht löslich in Anilin und Nitrobenzol.to derive bazoles. The condensation product of 2 · 4-dinitro-i-chlorobenzene and the leucoindophenol from IV ethyl carbazole and p-nitrosophenol is red-brown in color and crystallizes in small needles. The melting point is 223 °. It is very difficult to dissolve in Alcohol, glacial acetic acid, gasoline, chloroform and carbon tetrachloride, a little lighter in benzene, Easily soluble in aniline and nitrobenzene.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE252642C true DE252642C (en) |
Family
ID=510979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT252642D Active DE252642C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE252642C (en) |
-
0
- DE DENDAT252642D patent/DE252642C/de active Active
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