DE2519535A1 - ETHYLENE GLYCOL-2- (P-CHLOROPHENOXY) -2-METHYLPROPIONATE-NICOTINATE AND THE METHOD OF ITS MANUFACTURING - Google Patents
ETHYLENE GLYCOL-2- (P-CHLOROPHENOXY) -2-METHYLPROPIONATE-NICOTINATE AND THE METHOD OF ITS MANUFACTURINGInfo
- Publication number
- DE2519535A1 DE2519535A1 DE19752519535 DE2519535A DE2519535A1 DE 2519535 A1 DE2519535 A1 DE 2519535A1 DE 19752519535 DE19752519535 DE 19752519535 DE 2519535 A DE2519535 A DE 2519535A DE 2519535 A1 DE2519535 A1 DE 2519535A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorophenoxy
- ethylene glycol
- formula
- ester
- iii
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
PRT-'i-'TIG · ι^ΛΑ^ - PZILERPRT-'i-'TIG · ι ^ ΛΑ ^ - PZILER
cc jC F/C.-.Λ.:-.:.-.^ 40cc jC F / C .-. Λ.: -.: .-. ^ 40
SCHLQi33HcI1VIERSTH. 299SCHLQi33HcI 1 FOURST. 299
Äthylenglycol-2-(p-chlorphenoxy)-2-methylpropionat-nikotinat und Verfahren zu seiner Herstellung Ethylene glycol 2- (p-chlorophenoxy) -2-methylpropionate nicotinate and process for its preparation
Die Erfindung betrifft einen neuen Mischaster des Äthylenglycols und ein Verfahren zu seiner Herstellung.The invention relates to a new mixed master of ethylene glycol and a method for its production.
Der neue Mischester entspricht der FormelThe new mixed ester corresponds to the formula
(D VH/(D VH /
CH3 CH 3
und kann als Äthylenglycol-2-(p-chlorphenoxy)-2-methylpropionatnikotinat bezeichnet werden.and can be used as ethylene glycol 2- (p-chlorophenoxy) -2-methylpropionate nicotinate are designated.
Das Verfahren zur Herstellung des neuen Mischesters erfolgt nach folgendem Reaktionsschema:The process for producing the new mixed ester is carried out according to the following reaction scheme:
509849 /P968509849 / P968
CH.CH.
Cl-ZQV-O-C-COOMe + ClCH2-CH2OHCl-ZQV-OC-COOMe + ClCH 2 -CH 2 OH
CH-(ID ό CH- (ID ό
(III)(III)
CH.CH.
0-C-COOCH2-CH2OH0-C-COOCH 2 -CH 2 OH
(III) +(III) +
N.N.
ClCl
CH.CH.
-0-C-COOCH2-CH2OOC-0-C-COOCH 2 -CH 2 OOC
Durch die Umsetzung gemäß diesem Reaktionsschema erhält man das Produkt (I) in hoher Ausbeute.The reaction according to this reaction scheme gives the product (I) in high yield.
In der ersten Stufe wird ein Salz der 2-(p-Chlorphenoxy)-2-methylpropionsäure der Formel (II), in der Me Li, Na oder K bedeuten kann, mit Äthylenchlorhydrin, das sowohl als Reagens als auch als Lösungsmittel dient, umgesetzt. Diese Umsetzung ergibt den 2-(-Chlorphenoxy) -2-methylpropionsäureäthylenglycolester der Formel (III) in einer Ausbeute von 91 %. Die zweite Stufe besteht in der Umsetzung des Esters (III) mit Nikotinsäurechlorid in einem inerten Lösungsmittel, wie Chloroform, und in Gegenwart einer Base, wie Triäthylamin. Die Reinigung des Endproduktes (I) erfolgt vorteilhafterweise durch mehrmaliges Waschen mit Wasser und verdünnter Salzsäure, wobei ein analysenreines Produkt in einer Ausbeute von 75,1 % erhalten wird. Andere inerte Lösungsmittel und andere Basen können, wie dem Durchschnittsfachmann ohne weiteres ersichtlich, gleichfalls verwendet werden.In the first stage, a salt of 2- (p-chlorophenoxy) -2-methylpropionic acid is used of formula (II), in which Me can mean Li, Na or K, with ethylene chlorohydrin, which is used both as a reagent as also serves as a solvent, implemented. This reaction gives the 2 - (- chlorophenoxy) -2-methylpropionic acid ethyl glycol ester Formula (III) in a yield of 91%. The second stage consists in the reaction of the ester (III) with nicotinic acid chloride in one inert solvents such as chloroform, and in the presence of a base such as triethylamine. Purification of the end product (I) is advantageously carried out by washing several times with water and dilute hydrochloric acid, with an analytically pure product in a yield of 75.1% is obtained. Other inert solvents and other bases can be used, as one of ordinary skill in the art readily apparent, can also be used.
Der erfindungsgemäße Mischester (I) hat sich als wertvolles hypolipidämisches Mittel erwiesen.The mixed ester (I) of the present invention has been found to be a valuable hypolipidemic agent.
Die Erfindung wird durch das folgende Beispiel weiter veranschaulicht. The invention is further illustrated by the following example.
9849/09689849/0968
Herstellung des
1 ~/_2~ (p-Chlorphenoxy) -2-methylpropionat/- Manufacture of the
1 ~ / _2 ~ (p-chlorophenoxy) -2-methylpropionate / -
2-nikotinat-äthylenglycol-Mischesters2-nicotinate-ethylene glycol mixed ester
A. Herstellung des 2-(p-Chlorphenoxy)-2-methylpropionsäureäthylenglycolesters: A. Preparation of 2- (p-chlorophenoxy) -2-methylpropionic acid ethylene glycol ester:
Eine Lösung von 64,2 g 2-(p-Chlorphenoxy)-2-methylpropionsaure in 300 ml 1 η Natriumhydroxid wird im Vakuum bis zur Trockne eingedampft. Eine Suspension des erhaltenen Natriumsalzes in 300 ml Äthylenchlorhydrin wird 3 Stunden zum Sieden unter Rückfluß erhitzt. Danach wird der Überschuß an Chlorhydrin im Vakuum entfernt, wodurch das Reagens fast vollständig zurückgewonnen wird. Das hinterbleibende öl wird mit 200 ml Wasser versetzt, und die Mischung wird mehrmals mit Methylenchlorid extrahiert. Nach Verdampfen des Lösungsmittels und Rektifikation des Rückstandes erhält man 70 g (91 %) des 2-(p-Chlorphenoxy)-2-methylpropionsäureäthylenglycolesters mit einem Siedepunkt von 123 bis 125 0C bei 0,3 mm Hg.A solution of 64.2 g of 2- (p-chlorophenoxy) -2-methylpropionic acid in 300 ml of 1 η sodium hydroxide is evaporated to dryness in vacuo. A suspension of the sodium salt obtained in 300 ml of ethylene chlorohydrin is refluxed for 3 hours. Thereafter, the excess chlorohydrin is removed in vacuo, whereby the reagent is almost completely recovered. The remaining oil is mixed with 200 ml of water, and the mixture is extracted several times with methylene chloride. After evaporation of the solvent and rectification of the residue, 70 g (91%) of the 2- (p-chlorophenoxy) -2-methylpropionic acid ethylene glycol ester with a boiling point of 123 to 125 ° C. at 0.3 mm Hg are obtained.
B. Herstellung des Mischesters:B. Manufacture of the mixed ester:
Zu 25,85 g des 2-(p-ChIorphenoxy)-2-methylpropionsaure-äthylenglycolesters wird langsam eine Lösung von 15g Nikotinsäurechlorid in 60 ml Chloroform gegeben.To 25.85 g of the 2- (p-chlorophenoxy) -2-methylpropionic acid-ethylene glycol ester slowly becomes a solution of 15g nicotinic acid chloride given in 60 ml of chloroform.
Die Mischung wird 30 Minuten auf 50 0C erwärmt. Dann werden 16 ml Triäthylamin zugesetzt, und die Temperatur wird auf 60 0C erhöht und 2 Stunden bei diesem Wert gehalten. Die Mischung wird abgekühlt und mehrmals mit Wasser, 1 η Natriumhydroxid, Wasser und verdünnter Salzsäure gewaschen. Nach vollständigem Verdampfen des Lösungsmittels im Vakuum verbleiben 29,9 g (82,5 %) desThe mixture is heated to 50 ° C. for 30 minutes. Then 16 ml of triethylamine are added, and the temperature is increased to 60 ° C. and held at this value for 2 hours. The mixture is cooled and washed several times with water, 1 η sodium hydroxide, water and dilute hydrochloric acid. After the solvent has evaporated completely in vacuo, 29.9 g (82.5%) of des remain
509849/0968509849/0968
-if.-if.
Mischesters von Äthylenglycol mit 2-(p-Chlorphenoxy)-2-methylpropionsäure und Nikotinsäure, der durch Dünnschicht-Chromatographie, IR, NMR und Elementaranalyse identifiziert wird. Das Produkt siedet bei 214 0C bei 0,3 mm Hg unter Zersetzung.Mixed ester of ethylene glycol with 2- (p-chlorophenoxy) -2-methylpropionic acid and nicotinic acid, which is identified by thin-layer chromatography, IR, NMR and elemental analysis. The product boils at 214 ° C. at 0.3 mm Hg with decomposition.
Analyse für C18H18ClNO5:Analysis for C 18 H 18 ClNO 5 :
berechnet: C 59,43 %; H 4,99 %; N 3,85 %; gefunden: C 59,16 %; H 5,08 %; N 3,57 %.calculated: C 59.43%; H 4.99%; N 3.85%; found: C 59.16%; H 5.08%; N 3.57%.
509849/G968509849 / G968
Claims (7)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES426755A ES426755A1 (en) | 1974-05-29 | 1974-05-29 | Echirengurikooru 11*22*paraakurorofuenokishi**22 mechirupuropioneeto**22 nikochineeto kongoesuteruno seizohoho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2519535A1 true DE2519535A1 (en) | 1975-12-04 |
Family
ID=8466799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752519535 Pending DE2519535A1 (en) | 1974-05-29 | 1975-05-02 | ETHYLENE GLYCOL-2- (P-CHLOROPHENOXY) -2-METHYLPROPIONATE-NICOTINATE AND THE METHOD OF ITS MANUFACTURING |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS511479A (en) |
| DE (1) | DE2519535A1 (en) |
| ES (1) | ES426755A1 (en) |
| FR (1) | FR2272994A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2917014A1 (en) * | 1978-05-05 | 1979-11-15 | Alter Lab | AETHYLENE GLYCOL DIESTER AND METHOD FOR THE PRODUCTION THEREOF |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60222445A (en) * | 1984-04-19 | 1985-11-07 | Yoshitomi Pharmaceut Ind Ltd | Phthalic acid compound |
-
1974
- 1974-05-29 ES ES426755A patent/ES426755A1/en not_active Expired
-
1975
- 1975-04-28 FR FR7513271A patent/FR2272994A1/en active Granted
- 1975-05-02 DE DE19752519535 patent/DE2519535A1/en active Pending
- 1975-05-26 JP JP50063385A patent/JPS511479A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2917014A1 (en) * | 1978-05-05 | 1979-11-15 | Alter Lab | AETHYLENE GLYCOL DIESTER AND METHOD FOR THE PRODUCTION THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2272994A1 (en) | 1975-12-26 |
| JPS511479A (en) | 1976-01-08 |
| FR2272994B1 (en) | 1978-02-24 |
| ES426755A1 (en) | 1976-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |