CH143287A - Process for the preparation of a cyclammonium compound. - Google Patents
Process for the preparation of a cyclammonium compound.Info
- Publication number
- CH143287A CH143287A CH143287DA CH143287A CH 143287 A CH143287 A CH 143287A CH 143287D A CH143287D A CH 143287DA CH 143287 A CH143287 A CH 143287A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclammonium
- compound
- formula
- preparation
- product
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000004053 quinones Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000723347 Cinnamomum Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zimsatzpatent zum Hauptpatent Nr. 141551. Es wurde befunden, dass man eine Cyclammoniumverbindung erhalten kann. wenn man das Produkt der Formel
EMI0001.0004
in nicht alkalischem Medium mit Chinonen oxydiert und auf das gebildete Additions produkt mit dem ebenfalls entstandenen Hydrochinon Alkalien einwirken lässt.
Die hierbei ausgeschiedene Cyclammo- 'niumverbindung stellt ein in Wasser schwer lösliches, gelbbraunes Pulver dar. Dieses bildet durch Behandlung mit Säuren Salze der Formel
EMI0001.0011
die tannierte Baumwolle in rotvioletten Tö nen färben.
Beispiel: 427 Teile des Produktes der Formel
EMI0001.0013
werden in 2200 Teilen Benzol gelöst; und portionenweise innert einer Stunde mit 75 Teilen Eisessig und 1390 Teilen Chinon- lösung (10,7% Vol. Chi.non in Benzol) ver setzt. Zur Vervollständigung der Reaktion wird 15 bis 20 Stunden bei gewöhnlicher Temperatur gerührt und hierauf von den ab geschiedenen metallglänzenden Kristallen ab filtriert.
Die Untersuchung des erhaltenen Produktes lässt vermuten, dass ein Addi tionsprodukt von Hy drochinon an das 1 . 3 . 3 . 1'. 3' . 3'-Hexa.metliyl-5 . 5'-dichlor- 9. \?'-sirepl < @nionoviny 1 < >nindoeyaniance.tal: vor liegt. Der Körper löst sich leicht in heissem Wasser. Beim Versetzen der wässerigen Lösung mit verdünnter Natronlauge fällt die Cvclammoniumverbindung aus.
Cinnamon patent for main patent No. 141551. It has been found that a cyclammonium compound can be obtained. when you get the product of the formula
EMI0001.0004
oxidized with quinones in a non-alkaline medium and allowed to act on the addition product formed with the hydroquinone alkalis that were also formed.
The cyclammonium compound precipitated in the process is a yellow-brown powder that is sparingly soluble in water. This forms salts of the formula on treatment with acids
EMI0001.0011
dye the tannic cotton in red-violet tones.
Example: 427 parts of the product of the formula
EMI0001.0013
are dissolved in 2200 parts of benzene; and add 75 parts of glacial acetic acid and 1390 parts of quinone solution (10.7% vol. Chi.non in benzene) in portions within one hour. To complete the reaction, the mixture is stirred for 15 to 20 hours at ordinary temperature and then filtered off from the separated shiny metal crystals.
Examination of the product obtained suggests that an addition product of hydroquinone to the 1st 3. 3. 1'. 3 '. 3'-hexa.metliyl-5. 5'-dichloro- 9. \? '- sirepl <@nionoviny 1 <> nindoeyaniance.tal: is available. The body dissolves easily in hot water. When the aqueous solution is mixed with dilute sodium hydroxide solution, the ammonium compound precipitates.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH143287T | 1928-06-21 | ||
| CH141551T | 1928-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143287A true CH143287A (en) | 1930-10-31 |
Family
ID=25713892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143287D CH143287A (en) | 1928-06-21 | 1928-06-21 | Process for the preparation of a cyclammonium compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143287A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2734645A4 (en) * | 2011-07-18 | 2014-12-17 | Univ Georgia State Res Found | Carbocyanines for g-quadruplex dna stabilization and telomerase inhibition |
-
1928
- 1928-06-21 CH CH143287D patent/CH143287A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2734645A4 (en) * | 2011-07-18 | 2014-12-17 | Univ Georgia State Res Found | Carbocyanines for g-quadruplex dna stabilization and telomerase inhibition |
| US11572475B2 (en) | 2011-07-18 | 2023-02-07 | Georgia State University Research Foundation, Inc. | Carbocyanines for G-quadruplex DNA stabilization and telomerase inhibition |
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