CS265533B1 - 3-Acetyl-4 - [(2,3-epoxy) -propoxy] phenylcarbamic Acid Alkyl esters - Google Patents
3-Acetyl-4 - [(2,3-epoxy) -propoxy] phenylcarbamic Acid Alkyl esters Download PDFInfo
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- CS265533B1 CS265533B1 CS871891A CS189187A CS265533B1 CS 265533 B1 CS265533 B1 CS 265533B1 CS 871891 A CS871891 A CS 871891A CS 189187 A CS189187 A CS 189187A CS 265533 B1 CS265533 B1 CS 265533B1
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Abstract
Riešenie sa týká alkylesterov kyseliny 3-acetyl-4 Γ/2,3-epoxy/-propoxy| fenylkarbámovej všeobecného vzorca I, v ktorom R je alkyl s 3 až 4 atómami uhlíka, ako i spósobu výroby týchto látok a to reakciou alkylesteru kyseliny 3-acety1-4-hydroxyfenylkarbámovej s 3-chlór-l,2-epoxypropánom pri teplote miestnosti v prostředí hydroxidu alkalického kovu s výhodou hydroxidu draselného po dobu 6 h. Látky všeobecného vzorca I o hoře uvedenom význame R majú široké použitie ako východiskové suroviny pri príprave látok s biologickými účinkami.The solution concerns the alkyl esters of 3-acetyl-4 Γ/2,3-epoxy/-propoxy| phenylcarbamic acid of the general formula I, in which R is an alkyl with 3 to 4 carbon atoms, as well as the method of production of these substances by the reaction of the alkyl ester of 3-acetyl-4-hydroxyphenylcarbamic acid with 3-chloro-1,2-epoxypropane at room temperature in an alkali metal hydroxide environment, preferably potassium hydroxide, for 6 h. The substances of the general formula I with the above meaning of R have a wide use as starting raw materials in the preparation of substances with biological effects.
Description
265533
Vynález sa týká alkylesterov kyseliny 3-acetyl-4 £/2,3-epoxy/-propoxý]fenylkarbámovejvšeobecného vzorca I Z°\ :h-ch2coch3 (I) ,
NHCOOR kde R je alkyl s 3 až 4 atómami uhlíka, ako i spósobu pripravy týchto látok.
Zlúčeniny všeobecného vzorca I majú široké použitie ako východiskové suroviny ,pri prípravelátok s biologickými vlastnosťami (lokálně anestetické, betaadrenolytické, spazmolytickéa pod.) .
Látky Všeobecného vzorca I, v ktorom R znamená alkyl s 3 až 4 atómami uhlíka je možnépodlá vynálezu připravit tak, že sa nechá reagovat alkylester kyeliny 3-acetyl-4-hydroxy-fenylkarbámovej všeobecného vzorca II
COCHn
NHCOOR (II), v ktorom R znamená to isté ako vo vzorci I s 3-chlór-l,2-epoxypropánom pri teplote miestnostiv prostředí hydroxidu alkalického kovu s výhodou hydroxidu draselného po dobu 6 h. Látky všeobecného vzorca II o hoře uvedenom význame je možné připravit podlá prihl.vynálezu AO č. 158 638.
Bližšie podrobnosti o spósobe výroby látok podlá vynálezu vyplývajú z nasledujúcich príkladovprevedenia, ktoré však rozsah vynálezu neobmedzujú. Příklad 14,6 g (0,05 mol) propylesteru kyseliny 3-acetyl-4-hydroxyfenylkarbámovej sa rozpustív roztoku 3,3 g (0,06 mol) hydroxidu draselného v 100 ml vody a postupné sa přidá 5,5 g(0,06 mol) 3-chlór-l,2-epoxypropánu. Reakčná zmes sa mieša pri teplote miestnosti 6 h, produktsa vytrepe do éteru alebo benzénu, premyje vodou a 10 S roztokom hydroxidu sodného, vysušíbezvodým síranom horečnatým a po oddestilovaní rozpúšťadla sa produkt prekryštalizuje z.etanolu.Propylester kyseliny 3-acetyl-4 [/2,3-epoxy/-propoxy] fenylkarbámove j je bielá kryštalickálátka, vzniká vo výtažku 65 % teorie, t. t. 137 až 141 °C.
Elemen. anal. pre ci5Hi<)NO5! Vyp./náj. CHN 61,42/61,26 6,52/6,57 4,77/4,56 Příklad 2
Pracovný postup je ten istý ako v příklade 1, do reakcie se však použil butylester kyseliny 3-acetyl-4-hydroxyfenylkarbámovej, ktorý reakciou s 3-chlór-l,2-epoxypropánom poskytol butylester kyseliny 3-acety1-4 [/2,3-epoxy/-propoxy]fenylkarbámovej, ktorý sa prekryšta- lizuje z 2-propanolu. Je to bielá kryštalická látka, ktorá vzniká vo výtažku 68 % teorie, t. t. 125 až 128 °C.
265533
BACKGROUND OF THE INVENTION The present invention relates to alkyl esters of 3-acetyl-4- [2,3-epoxy] -propoxy] phenylcarbamate of the general formula IZ °: h-chloro-3 (I),
NHCOOR wherein R is alkyl of 3 to 4 carbon atoms, and a process for preparing such compounds.
The compounds of formula (I) have a wide variety of uses as feedstocks, in preparations with biological properties (locally anesthetic, betaadrenolytic, spasmolytic and the like).
Compounds of formula I wherein R is alkyl of 3 to 4 carbon atoms may be prepared by reacting the alkyl ester of 3-acetyl-4-hydroxy-phenylcarbamic acid of formula II
COCHn
NHCOOR (II) in which R is the same as in formula I with 3-chloro-1,2-epoxypropane at room temperature of an alkali metal hydroxide preferably potassium hydroxide for 6 h. can be prepared according to the invention AO No. 158 638.
Further details of the method for producing the compounds of the present invention will be apparent from the following non-limiting examples. Example 14.6 g (0.05 mol) of 3-acetyl-4-hydroxyphenylcarbamic acid propyl ester is dissolved in a solution of 3.3 g (0.06 mol) of potassium hydroxide in 100 ml of water and 5.5 g (0, 0) are added successively. 06 mol) of 3-chloro-1,2-epoxypropane. The reaction mixture was stirred at room temperature for 6 h, taken up in ether or benzene, washed with water and 10% sodium hydroxide solution, dried over anhydrous magnesium sulfate, and after distilling off the solvent, the product was recrystallized from ethanol. 3-epoxy-propoxy] phenylcarbamic acid is a white crystalline solid, m.p. 137-141 ° C (65%).
Elemen. anal. for c 15 H 11 NO 5! Vyp./náj. CHN 61.42 / 61.26 6.52 / 6.57 4.77 / 4.56 Example 2
The working procedure is the same as in Example 1, but 3-acetyl-4-hydroxyphenylcarbamic acid butyl ester was used in the reaction to give 3-acetyl-4-butylester butyl ester by reaction with 3-chloro-1,2-epoxypropane [/ 2,3] -epoxy-propoxy] phenylcarbamic acid which is recrystallized from 2-propanol. It is a white crystalline substance which is obtained in a yield of 68% of theory, m.p.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871891A CS265533B1 (en) | 1987-03-20 | 1987-03-20 | 3-Acetyl-4 - [(2,3-epoxy) -propoxy] phenylcarbamic Acid Alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871891A CS265533B1 (en) | 1987-03-20 | 1987-03-20 | 3-Acetyl-4 - [(2,3-epoxy) -propoxy] phenylcarbamic Acid Alkyl esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS189187A1 CS189187A1 (en) | 1989-02-10 |
| CS265533B1 true CS265533B1 (en) | 1989-10-13 |
Family
ID=5354420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS871891A CS265533B1 (en) | 1987-03-20 | 1987-03-20 | 3-Acetyl-4 - [(2,3-epoxy) -propoxy] phenylcarbamic Acid Alkyl esters |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS265533B1 (en) |
-
1987
- 1987-03-20 CS CS871891A patent/CS265533B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS189187A1 (en) | 1989-02-10 |
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