CS245091B1 - C-(4-azidophenyl)-n-phenylnitrone and method of its preparation - Google Patents
C-(4-azidophenyl)-n-phenylnitrone and method of its preparation Download PDFInfo
- Publication number
- CS245091B1 CS245091B1 CS852406A CS240685A CS245091B1 CS 245091 B1 CS245091 B1 CS 245091B1 CS 852406 A CS852406 A CS 852406A CS 240685 A CS240685 A CS 240685A CS 245091 B1 CS245091 B1 CS 245091B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- azidophenyl
- phenylnitrone
- preparation
- azidobenzaldehyde
- phenylhydroxylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- SDJOUGYEUFYPLL-UHFFFAOYSA-N 4-azidobenzaldehyde Chemical compound [N-]=[N+]=NC1=CC=C(C=O)C=C1 SDJOUGYEUFYPLL-UHFFFAOYSA-N 0.000 claims abstract description 6
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000003595 spectral effect Effects 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- -1 N-substituted hydroxylamines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
245091
Vynález sa týká C-(4-azidofenyl)-N-fenyl-nitrónu a sposobu jeho přípraVy.·^ ‘ V literatuře sú popísané rožne nitróny asposoby ich přípravy. Možno ich pripráVfí: — oxidáciou Ν,Ν-disubstituovaných hydro-xylamínov, — reakciou N-substituovaných hydroxyl-amínov s aldehydmi, — alkyláciou oxímov, — reakciou aromatických nitrózozlúče-nín a zlúčenín s aktívnou metylovou alebometylénovo>u skupinou.
Spektrálná citlivost takto připravenýchnitrónov bez azidoskupiny je priemerná.
Ns-^-CHO + (ζ^-NHOH- C-(4-azidofenyl)-N-fenylnitrón nie je v li-teratuře doteraz popísaný.
Jento nedostatok v podstatnej miere od-straňuje vynález, týkajúci sa C-( 4-azidof e-nyl j-N-fenylnitrónu a sposobu jeho přípra-vy.
Podstatou sposobu přípravy C-(4-azido-fenyl j-N-fenylnitrónu je, že na 4-azidobenz-aldehyd sa posobí N-fenylhydroxylamínemv rozpúšťadle, ako je metanol, etanol, pro-panol alebo ich zmesi, pri teplote 10 až 60°Celsia.
Reaikcia prebieha podlá všeobecnej sché-my:
V ďalšom je předmětný vynález objasněnýpríkladmi bez toho, že by sa na tieto vý-lučné vztahoval. Příklad 1 0,01 molu (1,09 g) N-fenylhydroxylamínučerstvo připraveného sa rozpustí v 10 mlmetanolu a přidá sa k němu po kvapkácha za miešania 0,01 molu (1,56 g) 4-azido-benzaldehydu. Po niekotkých minútach za-čne vypadávat kondenzačný produkt vo for-mě žitých kryštálov. Reakčná zmes sa po-nechá ešte stát pri teplote miestnosti nie-kofko hodin. Potom sa produkt odsaje, pre-myje metanolem alebo n-hexánom. V pří-pade potřeby sa prekryštalizuje. Výtažek je95 %-ný. Příklad 2 0,01 molu (1,09 gj čerstvo připravenéhoN-fenylhydroxylamínu sa rozpustí za teplav 10 ml etanolu. Potom sa k němu dávkuje0,01 molu (1,56 gj 4-azidobenzaldehydu roz-puštěného v 5 ml etanolu za miešania, pri-čom sa reakčná teplota udržuje pri 45 °C.Takmer okamžité začne sa z reakčnej zme-si vylučovat' žitý C-(4-azidof enyl)-N-f enyl-nitrón. Reakčná zmes sa mieša ešte 0,5 ho-diny pri teplote 20 °C a potom sa produktodsaje, premyje etanolem a vysuší. Výťažokje 98,5 %-ný. C-(4-azidofenyl)-N-f enylnitrometán podlávynálezu je látka sumárneho vzorca
C131H10N4O s molekulovou hmotnosťou 238,08 a teplotoutopenia 149 až 152 °C.
Jeho štruktúra bola dokázaná IČ, UV ahmotnostnou spektrometriou. IC spektrum bolo namerané na přístrojiSpecord IR 71 (Zeiss Jena) v CHCI3. Vykazu-je tieto charakteristiciké pásy (v cm-1): esa 2 100 (vn3), 1 505 (vc=n), 1210 (7n _ o). UV spektrum bolo namerané na přístrojiSpecord UV VIS (Zeiss Jena) v dioxáne priUV. Látka vykazuje dva pásy: pri λ = 268 nm (log ε = 3,90) a priλ = 348 nm (loge = 4,41).
Hmotnostně spektrum boto namerané na přístroji MS 902 S (AEI, Manchester). C-(4--azidofenyl)-N-fenylnitrón nedává v hmot-nostnom spekťre molekulový ión M+ 238, alelen fragment m/e 198 s relativnou intenzi-tou 25 %.
Analýza: vypočítané: 23,52 % N, 65,52 '% C, 4,23 % H, ZÍSt61161 23,30 % N, 65,04 % C, 4,19 % H. Výhodou látok podfa vynálezu je, že aro-matické nitróny obsahujúce azidovú skupinusa vyznačujú požadovanou spektrálnou cit-livosťou v blízkej ultrafialovej oblasti spek-tra. C-(4-azidofenyl)-N-fenylnitrón je svetlo- citlivá látka a možno· ju využiť na záznam optickej informácie do tenkých polymérnych vrstiev.
Claims (2)
- 245091 P R E D Μ E T 1. C-(4-azidofenyl j-N-fenylnitrón vzorca: Ng-^Q^-C Η ~ N --^Qy· O VYNÁLEZU
- 2. Sposob přípravy C-(4-azidofenyl)-N--fenylnitrónu podl'a bodu 1 vyznačujúci satým, že sa na N-fenylhydroxylamín působí4-azidobenzaldehydom v rozpúšťadle, akoje metanol, etanol, propanol alebo ich zmesi,pri teplete od 10 do 60 °C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS852406A CS245091B1 (en) | 1985-04-02 | 1985-04-02 | C-(4-azidophenyl)-n-phenylnitrone and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS852406A CS245091B1 (en) | 1985-04-02 | 1985-04-02 | C-(4-azidophenyl)-n-phenylnitrone and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS240685A1 CS240685A1 (en) | 1985-11-13 |
| CS245091B1 true CS245091B1 (en) | 1986-08-14 |
Family
ID=5361132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS852406A CS245091B1 (en) | 1985-04-02 | 1985-04-02 | C-(4-azidophenyl)-n-phenylnitrone and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS245091B1 (cs) |
-
1985
- 1985-04-02 CS CS852406A patent/CS245091B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS240685A1 (en) | 1985-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2323930C1 (ru) | Кристаллическая форма производного 1,2-дигидропиридина и способ ее получения | |
| DE69925032T2 (de) | Fluoreszenzfarbstoffe zum festphasen- und flüssigphasen-screening | |
| Petrovskaia et al. | Investigations of the reaction mechanisms of 1, 2-indanediones with amino acids | |
| Hay et al. | Substituent effects on the kinetics of reductively-initiated fragmentation of nitrobenzyl carbamates designed as triggers for bioreductive prodrugs | |
| MX2012015170A (es) | Derivados de 3-amino-5,6-dihidro-1h-pirazin-2-ona utiles para el tratamiento de la enfermedad de alzheimer y otras formas de demencia. | |
| Melloni et al. | Synthesis and antiprotozoal activity of methylnitro derivatives of 2, 2'-biimidazole | |
| CN101795727A (zh) | 作为钾通道调节剂的5-氨基-4,6-二取代吲哚和5-氨基-4,6-二取代二氢吲哚的衍生物 | |
| Zatsikha et al. | Functionalized bispyridoneannelated BODIPY–Bright long-wavelength fluorophores | |
| Hamdi et al. | Synthesis of some new biologically active coumarin derivatives | |
| CS245091B1 (en) | C-(4-azidophenyl)-n-phenylnitrone and method of its preparation | |
| Suwiński et al. | Nitroimidazoles XVII. Nucleophilic amination or ring transformation in reactions of 1-aryl-4-nitroimidazoles with 4-amino-1, 2, 4-triazole or hydroxylamine | |
| RU2685501C1 (ru) | Амидсодержащие производные 2-оксиндола, способ их получения и применения | |
| JP2012528119A (ja) | 分子間相互作用分析用の架橋試薬 | |
| AU627339B2 (en) | Novel cyclic vinylogous n-hydroxy-n-methylureas useful as 5-lipoxygenase inhibitors | |
| Lahiri et al. | Addition reactions of nucleophiles to dibenzoylacetylene | |
| Idocin et al. | Sydnonimines: synthesis, properties and applications in chemical biology | |
| Nikitjuka et al. | Synthesis and biological evaluation of aziridin-1-yl oxime-based vorinostat analogs as anticancer agents | |
| Anet et al. | A Synthesis of Hygrine and of Cuscohygrine | |
| Krayushkin et al. | Synthesis and spectral kinetic investigation of solutions of photochromic thienylfulgimides | |
| US20210333263A1 (en) | Redox activatable fluorescent sensors | |
| Seto et al. | The Formation of 1, 6-Dithia-3a-azonia-2, 3, 4, 5-tetrahydropentalene Salt | |
| SU1476856A1 (ru) | @ -Азидоциннамоилазины как светочувствительные компоненты фотополимеризующейс композиции | |
| Mishra et al. | Study and Characterization of Indole Carboxylate Derivative Synthesized Via Condensation | |
| Nawwar et al. | Oxazole, pyrazole and piperidine derivatives having an o-hydroxyaryl moiety with anticipated molluscicidal activity | |
| Gebretekle et al. | Synthesis and Biological Evaluation of Some Novel Hydrazones Carrying Benzimidazole and Pyrene/Vanillin Moiety |