CS265533B1 - Alkylesters of 3-acetyl-4/2,3-epoxy/-propoxy/phenylcarbamic acid and process for preparing thereof - Google Patents
Alkylesters of 3-acetyl-4/2,3-epoxy/-propoxy/phenylcarbamic acid and process for preparing thereof 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
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acetyl
- propoxy
- epoxy
- acid
- formula
- Prior art date
Links
- 239000004593 Epoxy Substances 0.000 title claims abstract description 7
- 125000005907 alkyl ester group Chemical group 0.000 title claims abstract 6
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- MJAGDKQQPLFBLI-UHFFFAOYSA-N (3-acetyl-4-hydroxyphenyl)carbamic acid Chemical compound CC(=O)C1=CC(NC(O)=O)=CC=C1O MJAGDKQQPLFBLI-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052751 metal Inorganic materials 0.000 claims abstract 2
- 239000002184 metal Substances 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 230000004071 biological effect Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 3-acetyl-4-butyl Chemical group 0.000 description 1
- PAUXAYKMCPEXKJ-UHFFFAOYSA-N C(CCC)OC(NC1=CC(=C(C=C1)O)C(C)=O)=O Chemical compound C(CCC)OC(NC1=CC(=C(C=C1)O)C(C)=O)=O PAUXAYKMCPEXKJ-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UGECVALOIRVFIG-UHFFFAOYSA-N propyl N-(3-acetyl-4-hydroxyphenyl)carbamate Chemical compound CCCOC(=O)Nc1ccc(O)c(c1)C(C)=O UGECVALOIRVFIG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 relates to alkyl esters of the acid 3-acetyl-4 '-( 2,3-epoxy) -propoxy phenylcarbamic acid of formula I wherein R is C 3 -C 4 alkyl as well as a process production of these substances by reacting the alkyl ester 3-acetyl-4-hydroxyphenylcarbamic acid with 3-chloro-1,2-epoxypropane at temperature room in alkaline hydroxide metal preferably potassium hydroxide after for 6 h. Compounds of Formula I on Mount as defined above, R have wide use as starting materials in the preparation of substances with biological effects.
Description
Vynález sa týká alkylesterov kyseliny 3-acetyl-4 £/2,3-epoxy/-propoxý]fenylkarbámovej všeobecného vzorca IThe present invention relates to 3-acetyl-4- (2,3-epoxy) -propoxy] phenylcarbamic acid alkyl esters of formula I
Z°\ :h-ch2 coch3 (I) ,Z ° \: h-ch 2 coch 3 (I),
NHCOOR kde R je alkyl s 3 až 4 atómami uhlíka, ako i spósobu pripravy týchto látok.NHCOOR wherein R is C 3 -C 4 alkyl, as well as a process for the preparation of these compounds.
Zlúčeniny všeobecného vzorca I majú široké použitie ako východiskové suroviny,pri príprave látok s biologickými vlastnostami (lokálně anestetické, betaadrenolytické, spazmolytické a pod.) .The compounds of the formula I have a wide application as starting materials in the preparation of substances with biological properties (locally anesthetic, beta-adrenolytic, spasmolytic and the like).
Látky Všeobecného vzorca I, v ktorom R znamená alkyl s 3 až 4 atómami uhlíka je možné podlá vynálezu připravit tak, že sa nechá reagovat alkylester kyeliny 3-acetyl-4-hydroxyfenylkarbámovej všeobecného vzorca IIThe compounds of the formula I in which R is a C 3 -C 4 alkyl can be prepared according to the invention by reacting the 3-acetyl-4-hydroxyphenylcarbamic acid alkyl ester of the formula II
NHCOORNHCOOR
COCH·· (II), v ktorom R znamená to isté ako vo vzorci I s 3-chlór-l,2-epoxypropánom pri teplote miestnosti v prostředí hydroxidu alkalického kovu s výhodou hydroxidu draselného po dobu 6 h.COCH ·· (II), wherein R is the same as in formula I with 3-chloro-1,2-epoxypropane at room temperature in an alkali metal hydroxide, preferably potassium hydroxide, environment for 6 h.
Látky všeobecného vzorca II o hoře uvedenom význame je možné připravit podlá prihl. vynálezu AO č. 158 638.The compounds of formula (II) as defined above can be prepared according to the invention. No. AO no. 158 638.
Bližšie podrobnosti o spósobe výroby látok podlá vynálezu vyplývajú z nasledujúcich príkladov prevedenia, ktoré však rozsah vynálezu neobmedzujú.The details of the process according to the invention are given in more detail by the following non-limiting examples.
PříkladExample
14,6 g (0,05 mol) propylesteru kyseliny 3-acetyl-4-hydroxyfenylkarbámovej sa rozpustí v 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, produkt sa vytrepe do éteru alebo benzénu, premyje vodou a 10 S roztokom hydroxidu sodného, vysuší bezvodým síranom horečnatým a po oddestilováni rozpúšťadla sa produkt prekryštalizuje z,etanolu. Propylester kyseliny 3-acetyl-4 [/2,3-epoxy/-propoxy] fenylkarbámove j je bielá kryštalická látka, vzniká vo výtažku 65 % teorie, t. t. 137 až 141 °C.14.6 g (0.05 mol) of 3-acetyl-4-hydroxyphenylcarbamic acid propyl ester are dissolved in a solution of 3.3 g (0.06 mol) of potassium hydroxide in 100 ml of water and 5.5 g (0, 06 mol) of 3-chloro-1,2-epoxypropane. The reaction mixture is stirred at room temperature for 6 hours, the product is taken up in ether or benzene, washed with water and 10% sodium hydroxide solution, dried over anhydrous magnesium sulphate and, after distilling off the solvent, the product is recrystallized from ethanol. 3-Acetyl-4 [(2,3-epoxy) -propoxy] -phenylcarbamic acid propyl ester is a white crystalline solid, yields in a yield of 65% of theory, m.p. t. M.p. 137-141 ° C.
Elemen. anal. pre ci5Hi<)NO5! Vyp./náj. C H NElemen. anal. for c i5 H i <) NO 5 ! Vyp./náj. CHN
61,42/61,2661.42 / 61.26
6,52/6,576.52 / 6.57
4,77/4,564.77 / 4.56
Příklad 2Example 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 prekryštalizuje z 2-propanolu. Je to bielá kryštalická látka, ktorá vzniká vo výtažku 68 % teorie, t. t. 125 až 128 °C.The procedure is the same as in Example 1, but 3-acetyl-4-hydroxyphenylcarbamic acid butyl ester was used in the reaction, which, by reaction with 3-chloro-1,2-epoxypropane, gave 3-acetyl-4-butyl ester [/ 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. t. Mp 125-128 ° C.
Elemen. anal. pre cigH2iN°5: Vyp./náj.Elemen. anal. for c ig H 2i N ° 5 : Off / Rent.
62,52/62,3262.52 / 62.32
6,88/6,756.88 / 6.75
4,55/4,544.55 / 4.54
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871891A CS265533B1 (en) | 1987-03-20 | 1987-03-20 | Alkylesters of 3-acetyl-4/2,3-epoxy/-propoxy/phenylcarbamic acid and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871891A CS265533B1 (en) | 1987-03-20 | 1987-03-20 | Alkylesters of 3-acetyl-4/2,3-epoxy/-propoxy/phenylcarbamic acid and process for preparing thereof |
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 | Alkylesters of 3-acetyl-4/2,3-epoxy/-propoxy/phenylcarbamic acid and process for preparing thereof |
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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