CS196930B1 - Metylester kyseliny 2-brómmetyl-3-(2-furyl)akrylovéj a sposob jeho přípravy - Google Patents
Metylester kyseliny 2-brómmetyl-3-(2-furyl)akrylovéj a sposob jeho přípravy Download PDFInfo
- Publication number
- CS196930B1 CS196930B1 CS2278A CS2278A CS196930B1 CS 196930 B1 CS196930 B1 CS 196930B1 CS 2278 A CS2278 A CS 2278A CS 2278 A CS2278 A CS 2278A CS 196930 B1 CS196930 B1 CS 196930B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acrylic acid
- furyl
- bromomethyl
- methyl ester
- acid methyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 title 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 18
- DAQJLFCNVBLQJR-UHFFFAOYSA-N methyl 2-(bromomethyl)-3-(furan-2-yl)prop-2-enoate Chemical compound COC(=O)C(CBr)=CC1=CC=CO1 DAQJLFCNVBLQJR-UHFFFAOYSA-N 0.000 claims description 17
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 methyl 2-bromomethyl-3- (2-furyl) acrylic acid Chemical compound 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229960002317 succinimide Drugs 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- WUWDAOLJZHBHPV-UHFFFAOYSA-N methyl 3-(furan-2-yl)-2-methylprop-2-enoate Chemical compound COC(=O)C(C)=CC1=CC=CO1 WUWDAOLJZHBHPV-UHFFFAOYSA-N 0.000 claims 1
- 238000004611 spectroscopical analysis Methods 0.000 claims 1
- 229940094989 trimethylsilane Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- FVGQQMFIAJTLMJ-UHFFFAOYSA-N ethyl 3-(furan-2-yl)-2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=CC1=CC=CO1 FVGQQMFIAJTLMJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ÚŘAD PRO VYNÁLEZYA OBJEVY ČESKOSLOVENSKÁ SOCIALISTICKÁ
REPUBLIKA POPIS VYNÁLEZU 196930 (11] (Bl) (51) Int. Cl.3 C 07 D 307/38 K AUTORSKÉMU OSVĚDČENÍ — (21) (PV 22-78) (22) Přihlášené 02 01 78 (40) Zverejnené 31 07 79 (45) Vydáno 30 11 81 (75)
Autor vynálezu
ŽVAK VLADIMÍR ing. a KOVÁČ JAROSLAV prof. ing. DrSc., BRATISLAVA (54) Metylester kyseliny 2-brómmetyl-3-(2-furyl) akrylovéj a sposob jeho přípravy
Vynález sa týká metylesteru kyseliny 2-bróm-metyl-3-(2-furyl) akrylové j a spósobu Jeho pří-pravy. 2-Halogénmetyl deriváty kyseliny 3-(2-fu-ryljakrylovej sú vhodné ako východiskové pro-dukty pre celý rad syntéz nových derivátov ky-seliny 2-X-3-(5-nitro-2-furyl)akrylovej s před-pokládanou biologickou účinnosťou, ktoré niesú z dostupnej literatury známe.
Tieto nedostatky v podstatnej miere odstra-ňuje vynález týkajúci sa metylesteru kyseliny2-brómmetyl-3- (2-Turyl) akrylové j.
Podstata sposobu přípravy metylesteru kyse-liny 2-brómmetyl-3-(2-furyl)akrylovej podlávynálezu spočívá v chemicky iniciované] selek-tívnej bromácii metylu na dvojnej vSzbe metyl-esteru kyseliny 2-metyl-3-(2-furyl)akrylovej N--brómsukcínimidom. Reakcia sa uskutočňujev bezvodom chloride uhličitom za přítomnostiiniciátora a, a - azobisizobutyronitrilu pri tep-lotě varu chloridu uhličitého.
Reakcia prebieha podlá schémy:
CHt— G0. N—Br !ΗΜ-βΟΖ GHjtBr GH-G^ XC00GMs Výhody spósobu přípravy metylesteru kyseli-ny 2-brómmetyl-3-(2-furyl)akrylovej podlá vy-nálezu spočívajú okrem iného v tom, že je jed-noduchý, ekonomický a lahko preveditelný.
Predmet vynálezu ilustruje, ale neobmedzujenasledovný příklad prevedenia reakcie. Příklad Příprava metylesteru 2-brómmetyl-3-(2-furyl)-akrylovej kyseliny.
Claims (2)
1. Metylester kyseliny 2-brómmetyl-3-(2-fu-ryl)akrylovej vzorca
COOCH»
2. Spůsob přípravy metylesteru kyseliny 2-brómmetyl-3-( 2-f uryl) akrylovej podfa bodu1, vyznačujúci sa tým, že metylester kyseli-ny 2-metyl-3-(2-furyl) akrylovej vzorca ^GHj, GH=\ \COOCHa
sa radikálovo brómuje N-brómsukcínimi-dom v prostředí chloridu uhličitého za ini-ciáce a, a‘-azobisizobutyronitrilu pri teplo-tě varu chloridu uhličitého.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS2278A CS196930B1 (cs) | 1978-01-02 | 1978-01-02 | Metylester kyseliny 2-brómmetyl-3-(2-furyl)akrylovéj a sposob jeho přípravy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS2278A CS196930B1 (cs) | 1978-01-02 | 1978-01-02 | Metylester kyseliny 2-brómmetyl-3-(2-furyl)akrylovéj a sposob jeho přípravy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196930B1 true CS196930B1 (cs) | 1980-04-30 |
Family
ID=5331657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS2278A CS196930B1 (cs) | 1978-01-02 | 1978-01-02 | Metylester kyseliny 2-brómmetyl-3-(2-furyl)akrylovéj a sposob jeho přípravy |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS196930B1 (cs) |
-
1978
- 1978-01-02 CS CS2278A patent/CS196930B1/cs unknown
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