It is commonly used to deprotonate moderately acidic protons such as phenols pka 10 and 1,3dicarbonyl compounds pka 9. The gabriel reaction has been generalized to include the alkylation of sulfonamides and imides, followed by deprotection, to obtain amines see. Potassium phthalimide is a chemical compound of formula c 8 h 4 kno 2. The carbonate can draw one hydrogen from two different water molecules. What is the mechanism of phthalimide synthesis from phthalic. The systematic procedure followed for the synthesis of target compounds is depicted in fig.
It is also used as an intermediate for synthetic indigo, pigments, dyes and pharmaceuticals. In this work, nbutylation of potassium phthalimide was carried out under. Pdf potassium phthalimide as efficient basic organocatalyst. Gabriel phthalimide synthesis mechanism the synthesis is used to get primary amines from primary alkyl halides and is named after the german scientist siegmund gabriel.
This technique is a safe and ecofriendly approach to the synthesis of different 4hchromens and 4hpyrans that offers many merits including short reaction times, high yields, straightforward workup, and no use of hazardous organic solvents. Recent strategies in organic reactions catalyzed by phase transfer catalysts and analyzed by gas chromatography 85 and ion chromatography identify inorganic anions by retention time or migration time. Potassium phthalimide suppliers exporters importers finoric. An improved procedure for the condensation of potassium. It is the potassium salt ofphthalimide, and usually presents as fluffy, very pale yellow crystals. Potassium phthalimidecatalysed onepot multicomponent. The two crops of crystals are united note 4 and washed with 200 cc. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. The xray analysis revealed the importance of substituents on the crystal stability and molecular packing. The mixture is gently boiled for about fifteen minutes or until no more of the phthalimide dissolves note 2. Organic molecules can have a higher level of complexity compared to inorganic compounds. By using our site, you agree to our use of cookies. The overlay structures were drawn using olex2 software 9.
Potassium carbonate can work as a base by creating potassium hydroxide by the break down of carbonate into carbon dioxide and water. Potassium phthalimide as efficient basic organocatalyst. Phthalimide potassium salt 98% potassium phthalimide sigma. Synthesis, structural and antioxidant studies of some novel n.
The solid material on the filter consists of some potassium bromide, some phthalimide, and the ethyl phthalimidomalonate. The gabriel synthesis, named for the german chemist siegmund gabriel, is a chemical reaction that transforms primary alkyl halides into primary amines using potassium phthalimide. It is used as an intermediate for the synthesis of synthetic indigo, pesticides, pigments, dyes and pharmaceuticals. Further, the molecular structure of majority of compounds were analysed by single crystal xray diffraction studies. The potassium salt is the reagent used in the gabriel synthesis. Phthalimide potassium salt was employed as organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions. Sigmaaldrich offers a number of phthalimide potassium salt products.
Other syntheses of phthalimideprotected amino groups. Nevertheless, a sample contaminated with matrix is often difficult to analyze. A convenient, efficient, and selective nalkylation of nacidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. Frequent shaking is necessary, and the sublimed material must be pushed back occasionally into the reaction flask. A series of dihydropyrano3,2cchromene derivatives were obtained via treating cyano methylene compounds malononitrile or ethyl cyanoacetate, aromatic aldehydes, and 4hydroxycoumarin in the presence of potassium phthalimide, as a green, mild, efficient, and commercially available organocatalyst in aqueous media. Gabriel synthesis generally fails with secondary alkyl halides. Finoric, etymologically derived from our business line of fine inorganic, organic and industrial chemicals, is the internationally preferred source for chemicals. It is the potassium salt of phthalimide, and usually presents as fluffy, very pale yellow crystals. It has been utilized as a reagent in the synthesis of primary amines by the gabriel method, and the synthesis of phthalimide derivatives.
Phthalimide is sufficiently acidic to form a potassium salt by treatment with concentrated potassium hydroxide solution. Phthalimide potassium salt ppi is widely used for the synthesis of primary amines from corresponding alkyl halides, known as gabriel synthesis. Organic synthesis is a special part of chemical synthesis. Potassium phthalimide ppi is a mild, green, inexpensive. Synthesis of n,oacetals by net amide cn bond insertion. Dec 18, 20 a series of dihydropyrano3,2cchromene derivatives were obtained via treating cyano methylene compounds malononitrile or ethyl cyanoacetate, aromatic aldehydes, and 4hydroxycoumarin in the presence of potassium phthalimide, as a green, mild, efficient, and commercially available organocatalyst in aqueous media. All the synthesized compounds were tested for in vitro.
Potassium phthalimide supplier and manufacturers represantative. Potassium phthalimide is a pale green powder chemical which is completely soluble in water. The journal of organic chemistry 2004, 69 10, 35173525. Procedure is available in text book of practical organic chemistry by a. It builds organic compounds using organic reactions. Structure, properties, spectra, suppliers and links for.
Avantor is a trusted global partner to customers and suppliers in the life science, advanced technology and applied materials industries. A very neet way of preparing primary amines is by using gabriel synthesis. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Earlier attempts by evans and dehn to prepare several naryl derivatives 23 and later by scott and lutz to prepare some nalkyl derivatives by this reaction had been unsuccessful 4. Synthesis, molecular docking, and antiepileptic activity. The reaction of potassium phthalimide with halogenoalkanes.
This procedure was easily performed, which provides a straightforward route. Dec 11, 2019 phthalimide conjugated to an amide bond, has been of the interest in several drug discovery efforts 8,9,10 due to its wide biological activities. Why does potassium carbonate work as a base for the. Issn 23333553 online issn 00786209 print we use cookies to help understand how people use our website. Buy high quality potassium phthalimide 1074824 from carbosynth, your source for carbohydrates. First crosscoupling reaction of potassium aryltrifluoroborates with organic chlorides in aqueous media catalyzed by an oximederived palladacycle. Synthesis, structural and antioxidant studies of some novel nethyl. During the conventional gabriel condensation, potassium phthalimide and an organic halide are treated. Particularly in peptide synthesis, the choice of appropriate nblocking groups is a critical decision if racemization is to be avoided 6. The synthesis of arylsulfonylphthalimides and their reactions. Potassium phthalimide manufacturers suppliers msds sheet. B4, ayodhya kutir, yashasvi nagar, balkum road, thane400608, maharashtra, india. It has been found that potassium phthalimide ppi catalyse the knoevenagel condensation reaction of salicylaldehydes and activated.
The hot solution is decanted from any solid into a specially prepared solution of 30. Showroom organic compound,inorganic compound,organic. As part of an ongoing program, we decided to develop a simple and. Potassium phthalimide promoted green multicomponent. Synthesis, structural and antioxidant studies of some novel nethyl phthalimide esters article pdf available in plos one 103. The journal of organic chemistry 20, 78 11, 52735281. An improved procedure for the condensation of potassium phthalimide with organic halides. Potassium carbonate k2co3 is a commonly used base in organic chemistry. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. A series of nethyl phthalimide esters 4an were synthesized and characterized by spectroscopic studies. As our channel brand, vwr offers an integrated, seamless purchasing experience that is optimized for the way our. Research accounts in the field of organic chemistry and synthesis of.
Potassium phthalimide ppi is a mild, green, inexpensive, commercially available, efficient basic recyclable catalyst, and a stable reagent. Phthalimide conjugated to an amide bond, has been of the interest in several drug discovery efforts 8,9,10 due to its wide biological activities. Potassium phthalimide,potassium phthalimide powder manufacturers. Traditionally, the reaction uses potassium phthalimide. Review and cite organic chemistry synthesis protocol, troubleshooting and.
I try to synthesize primary amine from alkylbromide reacted with potassium. Potassium phthalimide sds msds sheet, suppliers and manufacturers represantative. If desired, it may be prepared by adding a hot solution of phthalimide to a solution of potassium hydroxide. In this manner, phthalimide, indole, benzimidazole, and succinimide can be successfully alkylated. The subsequent procedure is the same as when aqueous ammonia is used. What is the mechanism of phthalimide synthesis from. Potassium phthalimidecatalysed onepot multicomponent reaction for efficient synthesis of aminobenzochromenes in aqueous media article in chemical papers slovak academy of sciences 688. The development of stable but easily removable amine protecting groups continues to interest both synthetic organic and peptide chemists 25. Articles of potassium phthalimide are included as well. Pdf synthesis, structural and antioxidant studies of. Sar studies and the identification of novel vascular disrupting agents. Phthalimide potassium salt 98% potassium phthalimide. Potassium phthalimide ppi, a mild, green and commercially available organocatalyst used in the synthesis of a wide range of important bioactive compounds. Can anyone help me with a gabriel synthesis for making primary.
Microwave synthesis is fast, efficient, with low side products, and therefore, is keenly. Microwave energy caused a great development in modern organic synthesis because of its advantageous features 12. Dec 21, 2007 palladiumcatalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles. Currently, ptc is an important choice in organic synthesis and is widely. Two methods for the preparation of phthalimide, hive. So, the synthesis of organic compounds has developed into one of the most important parts of organic chemistry. It is used as a precursor to other organic compounds as a masked source of ammonia. It is used as an intermediate for the synthesis of synthetic indigo, pesticides, pigments, dyes. Potassium phthalimide ppi is a mild, green, inexpensive, commercially available, effective solid basic catalyst, and stable reagent. Gabriel phthalimide synthesis mechanism explanation and. Development of solid basic catalytic systems using the cost effective, clean, environmentally benign and commercially available catalysts has been a challenge in organic synthesis. Potassium phthalimide is used for the synthesis of nalkylated phthalimides which produce primary amines gabriel synthesis by the hydrolysis reaction.
Is there any software to predict frequency of ir for organic compounds. Potassium phthalimide is used as an intermediate in the synthesis of nalkylated phthalimides, which is involved in the preparation of primary amines gabriel synthesis by the hydrolysis reaction. With customers in 55 countries across 5 continents, we source and sell most chemicals. Synthesis, structural and antioxidant studies of some. The hnmr of phthalimide intermidate is precise with phthalimide peak and my. Preparation of phthalimidogold precatalyst for gold catalysis. Two methods for the preparation of phthalimide, hive novel. Synthesis, molecular docking, and antiepileptic activity of. Condensation of phthalimide potassium with organic halide in dimethylformamide has been reported. An efficient procedure for the synthesis of various 2imino2hchromene3carbonitriles, 2oxo2hchromene3carbonitriles as well as 2oxo2hchromene3carboxylic acids is reported. It can be prepared by adding a hot solution of phthalimide in ethanol to a solution of potassium hydroxide in ethanol. Potassium phthalimide as efficient basic organocatalyst for the synthesis of 3,4disubstituted isoxazol54hones in aqueous medium. Potassium phthalimide ppi is a mild, green, inexpensive, commercially.
It is used as a precursor to other organic compounds as a. The reaction is named after the german chemist siegmund gabriel. This method provides rapid access to phthalimides starting from readily available. This compound is a commercially available reagent used in the gabriel synthesis of amines. Conjugated small molecules with tailored electronic energy levels for use as acceptors in organic solar cells arthur d. Potassium phthalimide is used as an intermediate in the synthesis. Potassium phthalimide msds section 1 chemical product and company identification product name. It was also employed as reagent for the transformation of allyl and alkyl halides into protected primary amines. The gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Potassium phthalimide catalysed onepot multicomponent reaction for efficient synthesis of aminobenzochromenes in aqueous media article in chemical papers slovak academy of sciences 688. Potassium phthalimide promoted green multicomponent tandem. Further, potassium phthalimide is widely used as a raw material in the formulation of carvedilol drug. Later, potassium phthalimide was reported to interact with ptoluenesul.
Synthesis of alkyl aryl ketones, diketone compounds, and 2arylbenzobfurans. It can be used in the palladiumcatalyzed enantioselective synthesis of. Building blocks, carbonyl compounds, chemical synthesis, cyclic imides, organic building blocks more. There are two main areas of research fields within the. Organic synthesis simple english wikipedia, the free.
Site map careers events programs reach regulations contact us email subscription center tool box. Phthalimide potassium salt 1074824 carbosynth product. After stirring at 100 overnight, the mixture is cooled and. The result is one carbon dioxide molecule one water molecule and two hydroxide ions. Potassium phthalimide ppi is a stable, mild, green, inexpensive, commercially available, and efficient basic recyclable catalyst. In a onestep synthesis of aliphatic potassium acyltrifluoroborates kats from organocuprates, organolithium and organomagnesium reagents were readily transmetalated onto cui and coupled with a katforming reagent. Development of solid basic catalytic systems utilizing inexpensive, clean, environmentally benign, and commercially available catalysts has been a challenge in organic synthesis. In a palladiumcatalyzed oxidative carbonylation reaction for the synthesis of phthalimides, an imine and h 2 o, which are generated in situ from the condensation of aldehyde and amine, serve as selfsufficient directing group and nucleophile, respectively.
Potassium phthalimide is treated with base, then a primary alkyl halide, and then either hydrazine, acid, or base. The reaction is named after the german chemist siegmund gabriel, who first posited the synthesis with the aid of his partner, james dornbush. Search results for potassium phthalimide at sigmaaldrich. Recent strategies in organic reactions catalyzed by phase. When the amine is not readily accessible, the direct nalkylation of phthalimides with alcohols under mitsunobu conditions and of potassium phthalimide with. Material safety data sheet potassium phthalimide msds. For these reasons, other methods for liberating the amine from the phthalimide have been developed. The first technique often produces low yields or side products. The yield of airdried potassium phthalimide is 160180 g. Potassium phthalimide,potassium phthalimide powder. We operate in more than 30 countries and deliver an extensive portfolio of mission critical products, services and solutions. Potassium phthalimide is a chemical compound of formula c8h4kno2. Heller 1 from the reaction of potassium phthalimide and sulfonyl chlorides. Machine manufacturer,supplier,exporter of platinum compounds from india.
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