Synthesis of welldefined phthalimide monofunctional hyperbranched polyglycerols and its transformation to various conjugation relevant functionalities gyorgy kasza1, gergely kali2, attila domjan3, lilla petho4, gyorgyi szarka1 and bela ivan1 1polymer chemistry research group, institute of materials and environmental chemistry and. Design, synthesis, and evaluation of bitopic arylpiperazine. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Substituted phthalimide ac94377 is a selective agonist of the. What is the mechanism of phthalimide synthesis from phthalic. Naoh or hydrazine to form aliphatic primary amines. In particular, d3rselective ligands that can eliminate side effects associated with dopamine d2 receptor d2r therapeutics have been validated. Predict which of the following species is the most acidic, phthalimide or benzamide.
The dyeing behaviour and fastness properties of these dyes had been investigated. Microsoft word application of potassium phthalimide author. It is used as a precursor to other organic compounds as a masked source of ammonia. However, the high homology in signaling pathways and the sequence similarity between d 2 r. The title com pound has been characterized by elemental analysis, ftir, 1h and c nmr techniques. After 1520 minutes the mixture turns into a foam then the reaction is complete. Rapid and clean synthesis of phthalimide derivatives in hightemperature, high pressure. Usually, phthalimide is synthesized by carbon dioxide and. Through the optimization of reaction, phthalimide derivatives were obtained in excellent yields through facile onepot mild condition reaction of phthalic acid with aryl. A series of nsubstituted phthalimides was synthesized by a thermal reaction.
Maity college of pharmacy, ips academy, rajendra nagar, indore 452012 m. Reaction conditions were the mole ratio of phthalic anhydride to 15nurea 99. Combine fine powders of 70 g of phthalic anhydride with 23 g of urea, pour the mixture 1 l rbf, heat the mixture strongly. Solventfree nalkylation of phthalimide catalyzed by. If released to soil, phthalamide should have very high mobility. With a comparative study, bmimoh 1butyl3methyl imidazolium hydroxide exhibited the highest catalytic activity among the selected basic ionic liquids, which afforded a convenient, efficient and general protocol for nalkyl phthalimides. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. Rapid and clean synthesis of phthalimide derivatives in high. Phthalimide and nsubstituted phthalimides are an important class of compounds because they possess important biological activities including antiinflammatory activity 1, analgesic activity 2 and hypolipidemic activity 3, and also it is used in organic synthesis and other industrial fields such as in drugs synthesis for the. If desired, the phthalimide may be recrystallised from 1200 ml of industrial spirit.
Recent advances and future prospects of phthalimide. Synthesis of nsubstituted phthalimidoalkyl 1h1,2,3triazoles. View notes phthalimide from che 202 at american college of gastroenterology. Kinetics and mechanism of the cleavage of phthalimide in. Pdf synthesis of some nphthalimide amino acids derivatives and. Synthesis and hypoglycemic activity of some phthalimide derivatives s.
Pdf potassium phthalimide as efficient basic organocatalyst. Synthesis, spectral characterization and ligation of n2. Nsubstituted phthalimide analogs veena kathuria 1, dr. What is the mechanism of phthalimide synthesis from. Files available from the acs website may be downloaded for personal use only. The electronwithdrawing inductive of the two adjacent co. Synthesis and application of phthalimide disperse dyes. The crystal structure of l1 has been solved by direct methods and refined by fullmatrix least squares.
Nhalogensubstituted phthalimides, obtained by the interaction of phthalimide with chlorine and bromine, for example, c 8 h 4 o 2 nbr, are used in laboratory practice for the halogenation of organic compounds. It is used to make synthetic indigo and phthalocyanine pigments which have macrocyclic structure showing striking coloring features like porphyrins biopigments. Corresponding authors a department of polymer science and engineering, state key laboratory of coordination chemistry, collaborative innovation center of chemistry for life sciences, key laboratory of high performance polymer materials and technology nanjing university, ministry of education, school of chemistry and chemical engineering, nanjing university, nanjing 210093, p. Phthalimide compounds containing methoxy and nitro groups in the aromatic ring showed strong lox activity as compare to the presence of chloride and methyl groups in the ring. Two methods for the preparation of phthalimide rated as. The sulfenyl phthalimides are one of the oldest groups of fungicides and are effective, safe and persistent.
Pdf potassium phthalimide ppi is employed as an efficient and effective. It is used as a precursor to other organic compounds as a. Gabriel phthalimide synthesis results in the formation of 1 amine only. The initial purpose of this study was to determine if steric problems would account for the difference in the products obtained in the reaction of the nsubstitutedphthalimide with low and high molecular weight amines. The gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. A different type of product was obtained when 1,2diphosphinobenzene was added to acetylacetone in the presence of hcl. The subsequent procedure is the same as when aqueous ammonia is used. Huntingdon life sciences mak0978 sponsor reference number. Title the reaction between urea and phthalic anhydride under. The reaction is named after the german chemist siegmund gabriel. Synthesis, structure, and properties of nnitraminophthalimide. Synthesis of 4nitrophthalimide ma1phthalimide 80 g was added into mixed acid which prepared from fuming nitric acid 65%, 100 g and concentrated sulfuric acid 98%, 500 g at 10 c. A new method for preparing 15nlabeled phthalimide from the reaction between phthalic anhydride and 15nurea 99.
The gabriel reaction has been generalized to include the alkylation of sulfonamides and imides, followed by deprotection, to obtain amines see. N 2hydroxyethylphthalimide c10h9no3 cid 77499 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safetyhazardstoxicity information, supplier lists, and more. Reactions of nsubstituted phthalimides with nalkylamines. Two methods for the preparation of phthalimide, hive. Finally, the synthesized phthalimide was used to successfully modify the surface of talc. Wikimedia commons has media related to phthalimide. Covid19 is an emerging, rapidly evolving situation. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. Synthesis and anticonvulsant activity of some nsubstituted. The absorption maxima of the dyes were observed in the range 360 to 700. Recent advances and future prospects of phthalimide derivatives.
Substituted phthalimide ac94377 is a selective agonist of. Phthalimides article about phthalimides by the free. Volatilization of phthalamide may not be important from moist or dry soil surfaces. Traditionally, the reaction uses potassium phthalimide. Frequent shaking is necessary, and the sublimed material must be pushed back occasionally into the reaction flask. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. Cool down the mixture until it is warm and add 300 ml of hot water. A variety of phthalimide derivatives have been synthesised effectively in.
Phthalimide, thermal stability, microwave irradiation, solventfree reaction. B77mi10706captan 59 is cheaply made from the dielsalder adduct of butadiene and maleic anhydride, followed by conversion to the imide and reaction with trichloromethanesulfenyl chloride. The structure of this compound was established by xray diffraction and confirmed by 1 h, c, and 14 n nmr spectroscopy. Gabriel method 58,64 the synthesis of phthalimide derivatives. The synthesis of strontium aluminates, sral 2 o 4, doped with europium and dysprosium, sral 2 o 4. All of the synthesized intermediates and dyes have been characterized by ms, 1hnmr and ir analyses. Pdf reaction of phthalimide with polyethylenepolyamines. Nsubstitutedphthalimide analogs veena kathuria 1, dr. Phthalamides production and use as an intermediate in organic synthesis and as a laboratory reagent may result in its release to the environment through various waste streams. Title the reaction between urea and phthalic anhydride.
Subsequently, a series of nsubstituted phthalimides including alkyl 29, methyl ketone 1o14, carboxylic acid 15191, and acetate ester 2023 sub stituents of various chain lengths were synthesized. In particular, d 3 rselective ligands that can eliminate side effects associated with dopamine d 2 receptor d 2 r therapeutics have been validated. Phthalimide is prepared from phthalic anhydride and the carbonate of ammonium or ammonia. Solventfree synthesis of phthalimide under microwave. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. The structure of the product was assigned to the diphosphaadamantane 3 on the basis of the symmetry of its 1 h, ch, and 31 ph nmr spectra and the structure was confirmed by xray crystallography 64a. Gibberellin is a major plant hormone that regulates plant growth and development and is widely used as a plant growth regulator in agricultural production. So, either way, my theory about weak base is wrong here, since the deprotonated phthalimide is a strong base and good nucleophile. Potassium phthalimide is basically the same as saying insert name of deprotonated phthalimide here. Design, synthesis, molecular docking, and cholinesterase. Therefore, gabriel phthalimide synthesis is preferred for synthesizing primary amines. Design, synthesis, photophysical properties and phsensing.
The dopamine d3 receptor d3r is a proven therapeutic target for the treatment of neurological and neuropsychiatric disorders. Pdf in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step, through cyclocondensation of. Well, it is not just about anthranilic acid, but also about its derivatives, its reactivity and chemical behaviour, but most especially the book is about my efforts to use anthranilic acid as a starting. Upload files that contain viruses, corrupted files, or any other similar software or programs that may damage the operation of anothers computer. Solventfree nalkylation of phthalimide with alkyl halides catalyzed by basic ionic liquids was developed in this conmmunication. Potassium phthalimide as efficient basic organocatalyst for the synthesis of 3,4disubstituted isoxazol54hones in aqueous medium january 2017 journal of saudi chemical society 21s1. There is an increasing demand for functionlimited ga mimics due to the limitations on the agronomical application of ga to crops, including gas high cost of producing and its leading to the crops lodging.
Gabriel phthalimide synthesis mechanism, synthesis of primary. The gabriel reaction has been generalized to include the alkylation of sulfonamides and imides, followed by deprotection. Synthesis and hypoglycemic activity of some phthalimide. Transitionmetalfree multicomponent reactions involving arynes, isocyanides, and co 2 as the third component resulted in the formation of n substituted phthalimides in good yields, whereas the use of water as the third component furnished. Synthesis of phthalimide february 23, 2016 december 23, 2017 organic combine fine powders of 70 g of phthalic anhydride with 23 g of urea, pour the mixture 1 l rbf, heat the mixture strongly. Cmin, phthalimide showed good thermal stability of phthalimide under 150. Well, it is not just about anthranilic acid, but also about its derivatives, its reactivity and chemical behaviour, but most especially the book is about my efforts to use anthranilic acid. Inspired by the synthesis of phthalimides by the mcr of isocyanides and arynes with co2, we continued. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3. Synthesis of heterocycles from anthranilic acid and its. The mixture is gently boiled for about fifteen minutes or until no more of the phthalimide dissolves note 2. Nnitramino phthalimide r 2 nnhno 2 r 2 nh is phthalimide was synthesized by nitration of naminophthalimide with nitronium tetrafluoroborate. The two crops of crystals are united note 4 and washed with 200 cc.
What product would you expect to obtain from the reaction of one equivalent of propanol with phthalic anhydride. Pdf potassium phthalimide as efficient basic organocatalyst for. The methylation of this compound with diazomethane affords a mixture of n. Residue data were received in 1993, but no recommendations could be made for citrus fruits, apples, melons or lettuce because the information on gap was insufficient or did not match the conditions of the trials. The dopamine d 3 receptor d 3 r is a proven therapeutic target for the treatment of neurological and neuropsychiatric disorders. Imidazolepromoted synthesis of nsubstituted phthalimide from n. The hot solution is decanted from any solid into a specially prepared solution of 30. The objective of this study was to validate methods of analysis for the determination of folpet and the degradates phthalimide, phthalamic acid, phthalic acid, 2cyanobenzoic acid and benzamide in water and sediment taken from a representative microcosm.
All reagents and solvents were purchased at the highest commercial quality and used without further purification unless otherwise noted. The initial purpose of this study was to determine if steric problems would account for the difference in the products obtained in the reaction of the nsubstituted phthalimide with low and high molecular weight amines. Phthalimide article about phthalimide by the free dictionary. A very neet way of preparing primary amines is by using gabriel synthesis. Arancibia al et al the pharmaceutical and chemical journal, 2016, 34. Pages in category phthalimides the following 14 pages are in this category, out of 14 total.
Coreshell inversion by ph modulation in dynamic covalent micelles r. Gabriel phthalimide synthesis is method of preparation of aliphatic primary amine from phthalimide and alkyl halide. What links here related changes upload file special pages permanent link page information. Huntingdon life sciences mak0978 sponsor reference. The set processes form zwitterionic biradical intermediates 3, in which a proton transfer and an. Dec 30, 2017 three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. H carbonylation of benzoyl hydrazides with carbon monoxide shuxian qiu the state key laboratory of chemical oncogenomics and the key laboratory of chemical genomics, shenzhen graduate school of peking university, shenzhen, 518055 peoples republic of china. The yield of airdried potassium phthalimide is 160180 g. Photochemical reactions of naphthalimides with electron donors.
Intercept or attempt to intercept electronic mail not intended for you. Two methods for the preparation of phthalimide, hive novel. Full paper synthesis of pyridinium amphiphiles used for transfection and some characteristics of amphiphiledna complex formation arthur a. Department of pharmaceutical chemistry, delhi institute of pharmaceutical sciences and research. Phthalimides article about phthalimides by the free dictionary. Supplementary information pdf 564k crystal structure data cif 997k. Niyaz khan, kinetics and mechanism of alkaline hydrolysis of no aminophenyl phthalimide in the presence and absence of cationic micelles and sodium salts of aliphatic acids, progress in reaction kinetics and mechanism, 10. Three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components.
Nhydroxyethyl phthalimide pei was prepared by refluxing phthalic anhydride with ethanolamine. Synthesis, structure, and properties of nnitramino. Coreshell inversion by ph modulation in dynamic covalent. Synthesis of phthalimide disperse dyes and study on the. Pdf file of the applications of gabriel amine synthesis. Department of pharmaceutical chemistry, delhi institute of pharmaceutical sciences and research dipsar, sector3, pushp vihar, new delhi110017, india. Dithiocarbamate hybrids as new agents for treatment of alzheimers disease mehdi asadi department of medicinal chemistry, faculty of pharmacy and pharmaceutical sciences research center, tehran university of medical sciences, 1417653761 tehran, iran. This experiment only requires basic experimental skills and limited equipment. Phthalimide reacts with koh to form potassium phthalimide,which further racts with alkyl halide to form alkyl halide to form nalkyl phthalimide.
Practical synthesis of phthalimides and benzamides by a. Synthetic of phthalimides via the reaction of phthalic. Phthalimide, derived from phthalic anhydride with ammonium hydroxide by heating, is used in the synthesis of primary amines and amino acids. Upload files that contain software or other material protected by intellectual property laws or by rights of privacy of publicity unless you own or control the rights thereto or have received all necessary consents. Nnitraminophthalimide r 2 nnhno 2 r 2 nh is phthalimide was synthesized by nitration of naminophthalimide with nitronium tetrafluoroborate. Design, synthesis, photophysical properties and phsensing application of pyrimidinephthalimide derivatives. An ironcatalyzed route for the regioselective synthesis of 1,3 and 1,3,5substituted. Design, synthesis, molecular docking, and cholinesterase inhibitory potential of phthalimide. Folpet 041 explanation folpet was first evaluated in 1969, and most recently reevaluated in 1993. The reactivity of carbonate, triethylamine and triethanolamine toward pth could not be detected under the experimental. Phthalimide is highly acidic in nature due to it easily donate the proton and form water soluble salts with stronger bases.1045 1130 533 1475 864 630 1376 26 129 791 66 874 281 1302 924 1191 83 1548 991 1079 1161 1093 1053 328 821 523 1219 446 957 1294 949 397 1057