CH213907A - Process for the production of a condensation product. - Google Patents
Process for the production of a condensation product.Info
- Publication number
- CH213907A CH213907A CH213907DA CH213907A CH 213907 A CH213907 A CH 213907A CH 213907D A CH213907D A CH 213907DA CH 213907 A CH213907 A CH 213907A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- condensation product
- product
- indolinone
- condensation
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- SWOOKKQLYUQUDI-UHFFFAOYSA-N n-(hydroxymethyl)decanamide Chemical compound CCCCCCCCCC(=O)NCO SWOOKKQLYUQUDI-UHFFFAOYSA-N 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- UXEGAAMXGLSKPB-UHFFFAOYSA-N n-(hydroxymethyl)octanamide Chemical compound CCCCCCCC(=O)NCO UXEGAAMXGLSKPB-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- -1 zinc chloride Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Kondensationsproduktes. Es wurde gefunden, dass wertvolle Kon densationsprodukte entstehen, wenn man Ver- bindungen, welche eine Dioxydiphenylmethan- gruppierung folgender Art enthalten
EMI0001.0006
wobei R Wasserstoff oder Alkyl- bezw. Acyl- gruppen und X die Methylen- oder Karbonyl- gruppe bedeuten,
mit Methylolamiden von Carbonsäuren kondensiert.
Die Kondensation verläuft gut in An wesenheit von Kondensationsmitteln, z. B. von Säuren, wie Salzsäure und Schwefelsäure, oder von Salzen, wie Zinkchlorid, oder von wasserentziehenden Mitteln, wie Phosphortri- chlorid oder Phosphoroxychlorid.
Die auf die beschriebene Weise herstell- baren Produkte können als Heilmittel, ins besondere als Abführmittel oder als Zwischen produkte zu solchen verwendet werden. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Konden sationsproduktes, welches dadurch gekenn zeichnet ist, dass man Caprylsäure-N-methylol- amid auf 3,3-Di-p-oxyphenyl-indolinon-2 der Formel
EMI0001.0029
bei Gegenwart eines Kondensationsmittels ein wirken lässt.
Das Produkt ist in Natronlauge löslich und gibt mit Ferricyankali violette bis blaue Farbreaktion: <I>Beispiel:</I> 40 g 3,3-Di-p-oxyphenyl-indolinon-2, 60 g Zinkchlorid, 120 g Eisessig werden heiss ge löst und nach dem Abkühlen mit<B>22-65</B> g Caprylsäure-N-metliylolamid versetzt, das sich leicht in dein CTemiscli auflöst. Nach 24stün- digem Stehen bei Zimmertemperatur wird die Lösung in dünnem Strahl in die Mischung von 2000 cm' Wasser und 100 cm" konzen trierter Salzsäure einfliessen gelassen.
Die körnige Masse wird abgesaugt, gut mit Was ser gewaschen und getrocknet. Durch Auf lösen in Methylalkohol und Eingiessen in eine 2'/2 /oige Sololösung kann das Produkt von unverändertem 3,3-Di-p-oxyplieny 1-indolinon-2 befreit werden.
Sollte es noch neutrale Pro dukte, zum Beispiel überschüssiges Capryl- säure-N-metliylolaniid enthalten, so kann es in 2000 cm'' 1 o,'oiger Natronlauge gelöst und zur Entfernung der neutralen Bestand teile klar filtriert und eventuell zweimal finit Äther ausgeschüttelt werden. Dann wird wie der in 1000 cm' Wasser und 50 eins kon zentrierte Salzsäure eingerührt, abgesaugt und mit Wasser gewaschen.
Die Verbindung löst sich leicht in 1 ;-"iger Natronlage. Die Lösung schäumt und gibt mit Ferricyankali eine violette bis blaue Farbreaktion.
Das Beispiel kann in der Weise abgeän dert werden, dass man statt Zinkchlorid-Eis- essig als Lösungs- und Kondensationsmittel andere Stoffe, zum Beispiel konzentrierte Schwefelsäure, verwendet.
Process for the production of a condensation product. It has been found that valuable condensation products are formed when compounds containing a dioxydiphenylmethane grouping of the following type are used
EMI0001.0006
where R is hydrogen or alkyl or. Acyl groups and X denotes the methylene or carbonyl group,
condensed with methylolamides of carboxylic acids.
The condensation goes well in the presence of condensing agents such. B. of acids such as hydrochloric acid and sulfuric acid, or of salts such as zinc chloride, or of dehydrating agents such as phosphorus trichloride or phosphorus oxychloride.
The products that can be manufactured in the manner described can be used as medicinal products, in particular as laxatives, or as intermediate products. The subject of the present patent is a process for the production of a condensation product which is characterized in that caprylic acid-N-methylolamide is added to 3,3-di-p-oxyphenyl-indolinone-2 of the formula
EMI0001.0029
in the presence of a condensing agent can act.
The product is soluble in sodium hydroxide solution and gives violet to blue color reactions with ferricyanide potassium: <I> Example: </I> 40 g of 3,3-di-p-oxyphenyl-indolinone-2, 60 g of zinc chloride, 120 g of glacial acetic acid become hot and after cooling down, <B> 22-65 </B> g of caprylic acid-N-methylolamide are added, which dissolves easily in your CTemiscli. After standing for 24 hours at room temperature, the solution is allowed to flow in a thin stream into the mixture of 2000 cm of water and 100 cm of concentrated hydrochloric acid.
The granular mass is filtered off with suction, washed well with water and dried. The product can be freed from the unchanged 3,3-di-p-oxyplieny 1-indolinone-2 by dissolving in methyl alcohol and pouring it into a 2½% strength solution.
Should it still contain neutral products, for example excess caprylic acid-N-methylolaniide, it can be dissolved in 2000 cm '' 10 '' sodium hydroxide solution and filtered to remove the neutral components and possibly shaken out twice with finite ether . Then like that in 1000 cm 'of water and 50 one concentrated hydrochloric acid is stirred in, filtered off with suction and washed with water.
The compound dissolves easily in a 1% sodium hydroxide layer. The solution foams and gives a violet to blue color reaction with ferricyankali.
The example can be modified in such a way that, instead of zinc chloride-glacial acetic acid, other substances, such as concentrated sulfuric acid, are used as solvents and condensation agents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE311038X | 1938-10-31 | ||
| CH213907T | 1939-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH213907A true CH213907A (en) | 1941-03-31 |
Family
ID=25725517
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH226823D CH226823A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226826D CH226826A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226821D CH226821A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226820D CH226820A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226822D CH226822A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226815D CH226815A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226825D CH226825A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226824D CH226824A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH213907D CH213907A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
Family Applications Before (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH226823D CH226823A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226826D CH226826A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226821D CH226821A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226820D CH226820A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226822D CH226822A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226815D CH226815A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226825D CH226825A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
| CH226824D CH226824A (en) | 1938-10-31 | 1939-10-26 | Process for the production of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (9) | CH226823A (en) |
-
1939
- 1939-10-26 CH CH226823D patent/CH226823A/en unknown
- 1939-10-26 CH CH226826D patent/CH226826A/en unknown
- 1939-10-26 CH CH226821D patent/CH226821A/en unknown
- 1939-10-26 CH CH226820D patent/CH226820A/en unknown
- 1939-10-26 CH CH226822D patent/CH226822A/en unknown
- 1939-10-26 CH CH226815D patent/CH226815A/en unknown
- 1939-10-26 CH CH226825D patent/CH226825A/en unknown
- 1939-10-26 CH CH226824D patent/CH226824A/en unknown
- 1939-10-26 CH CH213907D patent/CH213907A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH226821A (en) | 1943-04-30 |
| CH226822A (en) | 1943-04-30 |
| CH226824A (en) | 1943-04-30 |
| CH226823A (en) | 1943-04-30 |
| CH226826A (en) | 1943-04-30 |
| CH226815A (en) | 1943-04-30 |
| CH226825A (en) | 1943-04-30 |
| CH226820A (en) | 1943-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Clutterbuck et al. | A Study of the Oxidation of the Ammonium Salts of Normal Saturated Fatty Acids and its Biological Signifiance | |
| CH213907A (en) | Process for the production of a condensation product. | |
| AT92388B (en) | Process for the preparation of aralkyl esters of benzylamine carboxylic acids. | |
| AT256844B (en) | Process for the preparation of new 6,11-dihydrodibenzo- [b, e] -thiepinen | |
| AT252912B (en) | Process for the preparation of 3-methylflavone-8-carboxylic acid and its esters | |
| DE748713C (en) | Process for the production of pellets of dioxydiphenylmethanes | |
| DE726431C (en) | Process for the preparation of arylides from ª ‰ -ketone carboxylic acids | |
| DE820302C (en) | Process for the production of a new collection of trimethyl acetic acid (pivalic acid) | |
| Christie | The oxidation of various unsaturated organic compunds by means of potassium persulphate, using silver nitrate as a catalyst | |
| CH211850A (en) | Process for the preparation of a phenanthrene derivative. | |
| CH245883A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| CH142165A (en) | Process for the preparation of brominated 4,4'-dimethyl-6,6'-dichloro-thio-indigo. | |
| CH242287A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH124080A (en) | Process for the preparation of an organic rhodane compound. | |
| CH195775A (en) | Process for the preparation of a new ester. | |
| CH205163A (en) | Process for the preparation of a condensation product from trimethylhydroquinone and geranyl halide. | |
| CH263846A (en) | Process for the production of a chromating dye. | |
| CH264490A (en) | Process for the preparation of an acyl derivative of an acetoacetic acid amide. | |
| CH286681A (en) | Process for the preparation of -phenyl-butyric acid guajacol ester. | |
| CH207449A (en) | Process for the preparation of a condensation product. | |
| CH234955A (en) | Process for the preparation of the leuco sulfuric acid ester of a vat dye. | |
| CH180688A (en) | Process for the preparation of 2,4-dinitro-3,6-dichloroaniline. | |
| CH240392A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH206729A (en) | Method for the preparation of 5 ': 5 "- dibenzoylamino-1: 1': 5: 1" - trianthrimide carbazole. |