CS264191B1 - 3-/5-nitro-2-furyl/propenylbromid and process for preparing thereof - Google Patents
3-/5-nitro-2-furyl/propenylbromid and process for preparing thereof Download PDFInfo
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- CS264191B1 CS264191B1 CS877632A CS763287A CS264191B1 CS 264191 B1 CS264191 B1 CS 264191B1 CS 877632 A CS877632 A CS 877632A CS 763287 A CS763287 A CS 763287A CS 264191 B1 CS264191 B1 CS 264191B1
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- Prior art keywords
- furyl
- nitro
- propenyl
- bromide
- preparation
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- 238000004519 manufacturing process Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 22
- WRASENKOWNCZKM-UHFFFAOYSA-N C1=C(OC(=C1)[N+](=O)[O-])CC=CBr Chemical compound C1=C(OC(=C1)[N+](=O)[O-])CC=CBr WRASENKOWNCZKM-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 3- (5-nitro-2-furyl) propenyl Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000004071 biological effect Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 241000894006 Bacteria Species 0.000 abstract description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 2
- 230000000842 anti-protozoal effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- 230000015572 biosynthetic process Effects 0.000 description 2
- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical compound CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000195619 Euglena gracilis Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000223892 Tetrahymena Species 0.000 description 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Podstata sposobu prípravy3-(5-nitro- -2-furyl)propenylbromidu spočívá v tom, že sa na 3-(5-nitroi-2-furyl)propenylalkohol za chladenia působí bromačným činidlom v prostředí dietyléteru a vzniknutá reakčná zmes sa rozkládá s vodným roztokom hydroxidu alkalického kovu. Zlúčenina vykazuje biologická účinnost na baktérie a kvasinky a má antiprotozoálnu účinnost. Taktiež nájde široké využitíe v organické) syntéze pri príprave nových 3-(5-nitro-2-furyl)propenylových derivátov. 3-(5-nitro-2-furyl)propenylbromid podlá vynálezu je charakterizovaný vzorcom I.The nature of the preparation process3- (5-nitro- -2-furyl) propenyl bromide is that to 3- (5-nitro-2-furyl) propenyl alcohol; cooling acts with the brominating agent v diethyl ether and the resulting reaction the mixture is decomposed with an aqueous hydroxide solution alkali metal. The compound has biological activity on bacteria and yeast and has antiprotozoal activity. also, will find widespread use in organic synthesis to prepare new 3- (5-nitro-2-furyl) propenyl Derivatives. 3- (5-nitro-2-furyl) propenyl bromide according to the invention is characterized formula I.
Description
Vynález sa týká 3-(5-nitro-2-furyl)propenylbromidu vyznačujúceho sa biologickou aktivitou a spůsobu jeho přípravy.The present invention relates to 3- (5-nitro-2-furyl) propenyl bromide characterized by biological activity and a process for its preparation.
V literatuře je len ypfmf.máló/Q.dkago^.týkajúcich sa přípravy-3-(5-nitro-2Jfurýl')propenylových derivátov. Z dostupnej literatúry je známa syntéza 3-(5-nitro-2-furyl)propenylalkoholu a niekolkých jeho esterov (M. J. Berklava, S. Hillers: Latvijas PSR Zinatnu Akad. Vestis 3, 349 [1963]). Stádium literatúry ukázalo, že 3-(5-initro-2-furyl)propenylbromid nebol doteraz popísaný.In the literature only ypfmf.máló / Q.dkago ^ .týkajúcich was prepared 3- (5-nitro 2-furyl J ') propenylových derivatives. The available literature discloses the synthesis of 3- (5-nitro-2-furyl) propenyl alcohol and several esters thereof (MJ Berklava, S. Hillers: Latvijas PSR Zinatnu Akad. Vestis 3, 349 [1963]). The literature stage showed that 3- (5-initro-2-furyl) propenyl bromide has not been described so far.
Predmetom vynálezu je 3-(5-nitro-2-furyljpropenylbromid vzorca a sgdsoto jeho přípravy.The present invention provides 3- (5-nitro-2-furyl) propenyl bromide of the formula and its preparation.
Pqdstata sposobu přípravy 3-(5-nitro-2-furyl)propenylbromidu spočívá v tom, že na „3^5-'n1jro-2^lryl)propenylalkohol sa pósobí mromačným čiiďdlom ako bromid fosforitý, bromid fosforečný, kyselina bromovodíková, s výhodou bromid fosforitý, v prostředí dietyléteru v rozmedzí teplQt 0 až —20 CC, výhodné pri —10 °C, pričom vzniknutá reakčná zmes sa rozkládá s vodným roztokem hydroxidu alkalického kovu, s výhodou s roztokom hydroxidu draselného.The process for the preparation of 3- (5-nitro-2-furyl) propenyl bromide is characterized in that the "3 (5-nitro-2-yl) propenyl alcohol is treated with a refining agent such as phosphorus tribromide, phosphorus tribromide, hydrobromic acid, preferably phosphorus tribromide, in a diethyl ether medium, in the temperature range of 0 ° C to -20 ° C, preferably at -10 ° C, the resulting reaction mixture being decomposed with an aqueous alkali metal hydroxide solution, preferably potassium hydroxide solution.
Reakcia prebieha podfa schémy:The reaction proceeds according to the scheme:
(/(/
CH=CH-CH^Br (I)CH = CH-CH 2 Br (I)
Výhody spósobu přípravy 3-(5-nitr o-2-furyl)propenylbromidu podfa vynálezu spočívajú okrem iného v tom, že jeho příprava je jednoduchá, l'ahko prevediteTná, z dostupných surovin.Advantages of the process for the preparation of 3- (5-nitro-2-furyl) propenyl bromide according to the invention are, inter alia, that its preparation is simple, easy to convert from available raw materials.
Nasledujúci příklad bližšie ilustruje, ale neobmedzuje spósob přípravy zlúčeniny podfa vynálezu.The following example illustrates but does not limit the preparation of a compound of the invention.
PříkladExample
Příprava 3- (5-nitro-2-f uryl)propemylbromiduPreparation of 3- (5-nitro-2-furyl) propemyl bromide
K 0,1 molu (16,9 g) 3-(5-nitro-2-furylJpropenylalkoholu v 100 ml dietyléteru sa pri teplote —10 °C přidá 0,033 mólu (9,1 g) bromidu fosforitého v 20 ml dietyléteru. Zmes sa potom ešte mieša 30 min pri laboratórnej teplote. Reakčná zmes sa vyleje na 60 g 40percentného vodného roztoku hydroxidu draselného, ochladeného na —50 °C. Po intemzívnom premiešaní sa éterická vrstva oddělí a roztok hydroxidu draselného sa 3krát extrahuje s 50 ml dietyléteru. Spojené éterické extrakty sa premyjú vodou (3 X 15 mililitrov) a vysušia síranom sodným.To 0.1 mol (16.9 g) of 3- (5-nitro-2-furyl) propenyl alcohol in 100 mL of diethyl ether at -10 ° C was added 0.033 mol (9.1 g) of phosphorus tribromide in 20 mL of diethyl ether. The reaction mixture is poured onto 60 g of a 40% aqueous potassium hydroxide solution cooled to -50 [deg.] C. After intensive stirring, the ether layer is separated and the potassium hydroxide solution is extracted 3 times with 50 ml of diethyl ether. the extracts were washed with water (3 X 15 mL) and dried over sodium sulfate.
Po vákuovom oddestilování éteru sa 3-(5-nitro-2-furyl)propenylbromid prekryštalizuje z heptánu.After vacuum distilling off the ether, 3- (5-nitro-2-furyl) propenyl bromide is recrystallized from heptane.
Výťažok 15 g, t. j. 65,1 %.Yield 15 g, i.e. 65.1%.
3- (5-nitro-2-furyl) propeny lbromid podfa vynálezu je zlúčenina vzorca // (í)The 3- (5-nitro-2-furyl) propenyl bromide of the invention is a compound of formula // (i)
Sumárny vzorec zlúčeniny je C7H6BrNO3, molekufová hmotnost je 232,04 a t. t. 66 až 68 °C.The overall formula of the compound is C 7 H 6 BrNO 3, the molecular weight is 232.04 and mp 66-68 ° C.
Elementárna analýza vypočítanéElemental analysis calculated
6,05 % H, 34,5 % Br nájdené6.05% H, 34.5% Br found
6,08 % H, 34,58 % Br6.08% H, 34.58% Br
Štruktúra 3- (5-nitr o-2-f uryl) pr openylbromidu bola dokázaná IC a 1H NMR spektroskopiou. IC spektrá sa merali na spektrofotometr! UR-20 (fy Zeiss Jena) v chloroforme (koncentrácia 10-2 mólov). IČ spektrum 3- (5-nitr o-2-f uryl jpropenylbromidu vykazuje' tieto charakteristické pásy y (C—Hj = 962 cm1 vs (C—O—C) = 1016 cm“1 vs (NO2) = 1356 cm“1 vas (NO2) = 1 506 cm-1 v (C=C) =1571 cm-1 The structure of 3- (5-nitro-2-furyl) pr openyl bromide was shown by IC and 1 H NMR spectroscopy. IC spectra were measured on a spectrophotometer! UR-20 (Zeiss Jena) in chloroform (10 -2 mol concentration). The IR spectrum of 3- (5-nitro-2-furyl) propenyl bromide shows the following characteristic bands γ (C j H = 962 cm 1 vs (C O O C C) = 1016 cm -1 1 vs (NO 2) = 1356 cm -1) 1 as (NO2) = 1506 cm -1 v (C = C) = 1571 cm-1
4 1H NMR spektrum sa meralo ina spektrometri BS-487 C (fy Tesla Brno) v deuterovanom chloroforme, interný standard tetrametylsilán.4 1 H-NMR spectrum was measured ina spectrometer BS-487 C (from Tesla Brno) in deuterated chloroform, internal standard tetramethylsilane.
HjHj
CH2 dublet 4,11 ppmCH2 doublet 4.11 ppm
Ha dublet 6,49 ppmH and doublet 6.49 ppm
HB triplet, dubletu 6,71 ppmH B triplet, doublet 6.71 ppm
H3 dublet 6,52 ppmH3 doublet 6.52 ppm
H4 dublet 6,31 ppmH4 doublet 6.31 ppm
Výsledky testov ukázali, že 3-(5-nitro-2-furyljpropenylbromid podlá vynálezu vykazuje nevýrazná bakteriocídnu účinnost a vysokú antiprotozoálnu účinnost. Výsledky screeningu na niektoré kmene baktérií, kvasiniek a prvokov sú zhrnuté v tabulke 1.The results of the tests showed that the 3- (5-nitro-2-furyl) propenyl bromide according to the invention shows a low bacteriocidal activity and a high antiprotozoal activity.The screening results for some strains of bacteria, yeast and protozoa are summarized in Table 1.
Tabulka 1Table 1
Minimálna inhibičná koncentrácia (/xg/dísk)Minimum inhibitory concentration (/ xg / milks)
Vzhladom k tomu, že 3-(5-nitro-2-furyl)propenylbromid podlá vynálezu je zlúčenina dobré rozpustná v organických rozpúšťadlách a reaktívna voči nukleofilným činidlám, sprístupňuje syntézu nových 3-(5-nitro-2-furyljpropemylových derlvátov s předpokládanou biologickou účinnosťou.Since the 3- (5-nitro-2-furyl) propenyl bromide of the present invention is a compound well soluble in organic solvents and reactive to nucleophilic agents, it facilitates the synthesis of novel 3- (5-nitro-2-furyl) propenyl derivatives with the expected biological activity .
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877632A CS264191B1 (en) | 1987-10-26 | 1987-10-26 | 3-/5-nitro-2-furyl/propenylbromid and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877632A CS264191B1 (en) | 1987-10-26 | 1987-10-26 | 3-/5-nitro-2-furyl/propenylbromid and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS763287A1 CS763287A1 (en) | 1988-10-14 |
| CS264191B1 true CS264191B1 (en) | 1989-06-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS877632A CS264191B1 (en) | 1987-10-26 | 1987-10-26 | 3-/5-nitro-2-furyl/propenylbromid and process for preparing thereof |
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| Country | Link |
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| CS (1) | CS264191B1 (en) |
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1987
- 1987-10-26 CS CS877632A patent/CS264191B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS763287A1 (en) | 1988-10-14 |
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