CH125397A - Process for the preparation of di-O-isopropylphenolisatin. - Google Patents
Process for the preparation of di-O-isopropylphenolisatin.Info
- Publication number
- CH125397A CH125397A CH125397DA CH125397A CH 125397 A CH125397 A CH 125397A CH 125397D A CH125397D A CH 125397DA CH 125397 A CH125397 A CH 125397A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- isatin
- isopropylphenol
- preparation
- acetic acid
- Prior art date
Links
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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung von 1)i-O-isopropylplienolisatin. Bis jetzt wurde allgemein angenommen, dass die Wirkung plienolartiger Abführmittel mit dem Vorhandensein einer öder mehrerer freier "oder nur schwach blockierter IIy- droaylgruppen zusammenhängt (Kaufmann, Beitrag zur Theorie der @azantia. , Phar- maceutische Zeitung. No. 77, 1926. S. 1202).
Es hat sich nun überraschenderweise er geben, dass die All.:v1- und Aralkylderivate der Diphenolisatine, welche keine freie H-T- drozylgruppe mehr besitzen und auch nicht verseifbar sind. auso-ezeiclinet:e Abführmittel darstellen, die schon in sehr geringen Dosen eine gleichniässi;-e uiid sicbere Wirkung ent falten.
Die vorlien-eiide Erfindung bezieht sich auf ein Verfahren zur Darstellung des Di-0- isopropylphenolisatin s. welches dadurch ge kennzeichnet ist. dass man auf Diphenol- i@atin, dein die honstitutionsforinel
EMI0001.0033
zukommt. ein Isopropylhalogenid einwirken lässt. Nach diesem Verfahren kann man da.s Di-O-isopropylphenoliäatin in sehr guter Ausbeute und in reiner Form gewinnen.
Das Di-O-isopropylplienolisatin bildet bei <B>237</B> bis 238 schmelzende Kristalle. Es stellt eine neutral reagierende, sehr beständige Ver- bindung dar, welche mit Ferricyankalium und Natronlauge keine Farbreaktion mehr gibt. In Wasser, Alkalien und Säuren ist es unlöslich: in den üblichen organischen Lii- sungsmitteln, Alkohol, Benzol. Eisessig. löst es sich in der Wärme leicht.
Durch Acc- tvlierung geht es in das N-Acetyl-di-0-iso- propylphenolisatin vom Schmelzpunkt 145 bis 7.t6 über. Das Di-O-isopropylphenol- isatinsoll als Arzneimit@Lel verwendet werden.
<I>Beispiel:</I> 20 Teile Diphenolisatin #verden in einer Lösung von 5 Teilen Ätznatron und 100 Teilen Wasser gelöst und nach Zugabe von <B>15,6</B> Teilen Isopropylbromid zwei Stunden lang am Pückflusskühler erwärmt, wobei die Masse fest wird.
Nach dem Abkühlen wird filtriert. mit verdünnter Natronlauge ge-
EMI0002.0001
waschen <SEP> und <SEP> schliesslich <SEP> aus <SEP> Eisessig <SEP> umkri stallisiert. <SEP> Das <SEP> auf <SEP> diese <SEP> Weise <SEP> gewonnene
<tb> Di-O-isopropylphenolisatin <SEP> schmilzt <SEP> bei <SEP> 237
<tb> bis <SEP> 238 . <SEP> Durch <SEP> Acetvlieren <SEP> mit <SEP> Essigsäure -inhyclrid <SEP> und <SEP> \ <SEP> atriumacetat <SEP> erhält <SEP> man
<tb> (las <SEP> N' <SEP> Aeetyl-di-0-isopropylphenolisalin <SEP> vom
<tb> Si#linielzpunkt <SEP> 1-15 <SEP> bis <SEP> 1-1(i .
Process for the preparation of 1) i-O-isopropylplienolisatin. Until now it was generally assumed that the effect of plienol-like laxatives is related to the presence of one or more free or only weakly blocked hydroxyl groups (Kaufmann, contribution to the theory of @azantia., Pharmaceutische Zeitung. No. 77, 1926. p . 1202).
It has now surprisingly been found that the all: v1 and aralkyl derivatives of diphenolisatins which no longer have a free H-T drozyl group and are also not saponifiable. auso-ezeiclinet: e are laxatives which, even in very small doses, develop an equally effective and safer effect.
The present invention relates to a process for the preparation of di-0-isopropylphenolisatin. which is characterized by it. that one on Diphenol- i @ atin, your the honstitutionsforinel
EMI0001.0033
comes to. allows an isopropyl halide to act. This process can be used to obtain the di-O-isopropylphenolate in very good yield and in pure form.
The di-O-isopropylplienolisatin forms at <B> 237 </B> to 238 melting crystals. It represents a neutrally reacting, very stable compound which no longer reacts with ferricyanide and sodium hydroxide solution. It is insoluble in water, alkalis and acids: in the usual organic solvents, alcohol, benzene. Glacial acetic acid. it dissolves easily in the heat.
Accumulation converts it to N-acetyl-di-0-isopropylphenol isatin with a melting point of 145 to 7.t6. The di-O-isopropylphenol isatin is intended to be used as a medicament.
<I> Example: </I> 20 parts of diphenolisatin #verden dissolved in a solution of 5 parts of caustic soda and 100 parts of water and, after the addition of <B> 15.6 </B> parts of isopropyl bromide, heated for two hours in a reflux condenser, with the mass becomes solid.
After cooling, it is filtered. with dilute caustic soda
EMI0002.0001
wash <SEP> and <SEP> finally <SEP> from <SEP> glacial acetic acid <SEP> recrystallized. <SEP> The <SEP> won <SEP> this <SEP> way <SEP>
<tb> Di-O-isopropylphenolisatin <SEP> melts <SEP> at <SEP> 237
<tb> to <SEP> 238. <SEP> <SEP> Acetvlating <SEP> with <SEP> acetic acid arylide <SEP> and <SEP> \ <SEP> atrium acetate <SEP> gives <SEP>
<tb> (read <SEP> N '<SEP> Aeetyl-di-0-isopropylphenolisalin <SEP> from
<tb> Si # linielzpunkt <SEP> 1-15 <SEP> to <SEP> 1-1 (i.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH124026T | 1926-10-09 | ||
CH125397T | 1926-10-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH125397A true CH125397A (en) | 1928-04-16 |
Family
ID=25710180
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH125397D CH125397A (en) | 1926-10-09 | 1926-10-09 | Process for the preparation of di-O-isopropylphenolisatin. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH125397A (en) |
-
1926
- 1926-10-09 CH CH125397D patent/CH125397A/en unknown
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