3891-07-4

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Hydroxyethylphthalimide is used as a reagent for the synthesis of (-)-R-rolipram, a phosphodiesterase 4 inhibitor. N-Hydroxyethylphthalimide is utilized in the treatment of depression, as it helps regulate the levels of certain chemicals in the brain, thereby improving mood and overall mental health.
N-Hydroxyethylphthalimide is also used as a reagent in the synthesis of FR252921, a compound that acts as an immunosuppressant. This application is particularly relevant in the field of organ transplantation, as it helps prevent the body's immune system from attacking the transplanted organ.
Additionally, N-Hydroxyethylphthalimide serves as a precursor for chloromethyl ethers, which are used in the synthesis of purine acyclic nucleosides. These nucleosides have potential applications in the development of new drugs for various diseases, including cancer and viral infections.
Used in Chemical Research:
As a white crystalline powder with specific chemical properties, N-Hydroxyethylphthalimide is also used in chemical research and development. It can be employed as a starting material or intermediate in the synthesis of other complex organic compounds, contributing to the advancement of chemical knowledge and the creation of novel materials and pharmaceuticals.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 106, 1963The Journal of Organic Chemistry, 24, p. 1122, 1959 DOI: 10.1021/jo01090a601

InChI:InChI=1/C10H9NO3/c12-6-5-11-9(13)7-3-1-2-4-8(7)10(11)14/h1-4,12H,5-6H2

Upstream product

• 75-21-8 oxirane 
• 136918-14-4 phthalimide 
• 96-49-1 [1,3]-dioxolan-2-one 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 64-17-5 ethanol 
• 109-89-7 diethylamine 
• 1074-82-4 potassium phtalimide 
• 107-07-3 2-chloro-ethanol 
• 183969-33-7 9b-Ethoxy-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one 
• 65391-10-8 N-phthalimido-D,L-serine 
• 75-56-9 methyloxirane 
• 141072-57-3 1-bromoethanol 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 
• 97-60-9 2-acetamido-4-nitrophenol 

Downstream Products

• 4537-76-2 distearylphosphatidylethanolamine 
• 20255-95-2 dimyristoylphosphatidylethanolamine 
• 5466-90-0 2-(1,3(2H)-dioxo-1H-isoindol-2-yl)ethyl acetate 
• 6656-84-4 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl benzoate 
• 61318-34-1 propionic acid-(2-phthalimido-ethyl ester) 
• 13031-58-8 benzenesulfonic acid-(2-phthalimido-ethyl ester) 
• 5460-83-3 2-(1,3-dioxoisoindolin-2-yl)ethyl 4-methylbenzenesulfonate 
• 7507-15-5 stearic acid-(2-phthalimido-ethyl ester) 
• 3485-84-5 N-vinylphthalimide 
• 115610-20-3 (3aR,7aS)-2-(2-hydroxyethyl)-octahydro-1H-isoindole-1,3-dione 
• 5334-06-5 2-(2-hydroxyethyl)-2,3-dihydro-1H-benzo[c]pyrrol-1-on 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 4702-13-0 N-phthaloylglycine 
• 52198-45-5 Phosphorsaeuredichlorid-(2-phthalimidoethyl)ester 

Relevant academic research and scientific papers

Microgels as Matrices for Molecular Receptor and Reactive Sites: Synthesis and Reactivity of Cavities possessing Amino-functions

Non-fluxional polymeric particles, microgels, have been prepared containing amino-functions situated in cavities in the polymer matrix.The microgels possess binding properties and exhibit greatly enhanced rates of reaction versus isoquinoline-N-sulphonate and 4-nitrophenyl ester substrates compared with simple amines.The polymer reagents possess selectivity against the molecular size of the substrate due to finite cavity size and this selectivity may be modified by variation of pH which causes a change in size of the cavities.

Activities of 2-phthalimidethanol and 2-phthalimidethyl nitrate, phthalimide analogs devoid of the glutarimide moiety, in experimental models of inflammatory pain and edema

The reintroduction of thalidomide in the pharmacotherapy greatly stimulated the interest in the synthesis and pharmacological evaluation of phthalimide analogs with new and improved activities and also greater safety. In the present study, we evaluated the activities of two phthalimide analogs devoid of the glutarimide ring, namely 2-phthalimidethanol (PTD-OH) and 2-phthalimidethyl nitrate (PTD-NO), in experimental models of inflammatory pain and edema in male C57BL/6J mice. Intraplantar (i.pl.) injection of carrageenan (300 μg) induced mechanical allodynia and this response was inhibited by previous per os (p.o.) administration of PTD-OH and PTD-NO (750 mg/kg) and also by thalidomide (500 or 750 mg/kg). The edema induced by carrageenan was also inhibited by previous p.o. administration of PTD-OH (500 and 750 mg/kg) and PTD-NO (125, 250, 500 or 750 mg/kg), but not by thalidomide. Carrageenan increased tumor necrosis factor (TNF)-α and CXCL1 concentrations and also the number of neutrophils in the paw tissue. Previous p.o. administration of PTD-NO (500 mg/kg) reduced all the parameters, while PTD-OH (500 mg/kg) reduced only the accumulation of neutrophils. Thalidomide, on the other hand, was devoid of effect on these biochemical parameters. Plasma concentrations of nitrite were increased after p.o. administration of the phthalimide analog coupled to a NO donor, PTD-NO (500 mg/kg), but not after administration of PTD-OH or thalidomide. In conclusion, our results show that small molecules, structurally much simpler than thalidomide or many of its analogs under investigation, exhibit similar activities in experimental models of pain and inflammation. Finally, as there is evidence that the glutarimide moiety contributes to the teratogenic effect of many thalidomide analogs, our results indicate that phthalimide analogs devoid of this functional group could represent a new class of analgesic and anti-inflammatory candidates with potential greater safety.

Facile synthesis of indolizinoindolone, indolylepoxypyrrolooxazole, indolylpyrrolooxazolone and isoindolopyrazinoindolone heterocycles from indole and imide derivatives

Chemo-, regio- and diastereoselective coupling reactions of indole with imide derivatives leading to unique heterocyclic systems are demonstrated. Acid-induced 3-position coupling reactions of indole with cyclic imide derived lactamols followed by acid promoted 2-position cyclizations with the corresponding aldehydes are described to obtain the indolizinoindolones and benzoindolizinoindolones. Base induced 2-position coupling reactions ofN-tosylindole withN-(2-iodoethyl)imides and the subsequent cyclizations provide indolylepoxypyrrolooxazole, indolylpyrrolooxazolone and indolyloxazoloisoindolone. Reductive cleavage of indolyloxazoloisoindolone to the corresponding alcohol followed by mesylation and base promotedN-cyclization affords thein situair-oxidized pentacyclic product hydroxyisoindolopyrazinoindolone. A regioisomeric structural revision of the natural product from 1,2,5,6,7,11c-hexahydro-3H-indolizino[7,8-b]indol-3-one to 1,2,5,6,11,11b-hexahydro-3H-indolizino(8,7-b)indol-3-one is also reported in the present studies focussed on the methodologies for heterocyclic synthesis.

Novel synthesis method of N-hydroxyethyl phthalimide

The invention discloses a novel synthesis method of N-hydroxyethyl phthalimide, which comprises: by taking phthalimide and ethylene oxide as substrates, carrying out nucleophilic substitution reaction to enable the ethylene oxide to be subjected to ring opening, so as to prepare the N-hydroxyethyl phthalimide. According to the method, N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAC) is taken as a solvent, phthalimide and ethylene oxide are directly heated at 100-160 DEG C to react, the temperature is kept to react for a period of time, and then cooling and simple filtering are performed to obtain the N-hydroxyethyl phthalimide with the content of more than 99%. The molar yield can reach 97% or above. No by-product is generated in the whole synthesis production process; after being filtered, the solvent can be applied to the next batch of reaction without treatment, and no process waste is generated in the whole process, so that zero emission of organic synthesis is really realized, and the purpose of clean production is achieved.

FLUORINATED BENZO[F]BENZIMIDAZOL-4-9-DIONE IUM DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF AND THEIR USE AS SURVIVIN SUPPRESSANTS

The present application relates to novel fluorinated derivatives, to processes for their preparation, to compositions comprising them, and to their use in therapy. More specifically, it relates to compounds useful in the treatment of diseases, disorders or conditions mediated by survivin inhibition. In particular, the present application includes compounds of Formula (I) or (II), and compositions and uses thereof: (Formulae (I) (II)).

Synthesis method of 2-(phthalimido)ethanesulfonyl chloride

The invention discloses a synthesis method of 2-(phthalimido)ethanesulfonyl chloride. The specific reaction steps are as follows: (1) taking phthalic anhydride and ethanolamine as raw materials, and preparing to obtain N-(2-hydroxyethyl)phthalimide at appropriate temperature and in an appropriate solvent; (2) reacting the N-(2-hydroxyethyl)phthalimide synthesized in the step (1) with thiourea under appropriate temperature and solvent conditions, to obtain an isothiourea compound; (3) reacting the isothiourea compound synthesized in the step (2) under appropriate chlorination reagent, temperature and solvent conditions to obtain 2-(phthalimido)ethanesulfonyl chloride. A novel synthetic route is adopted to prepare 2-(phthalimido)ethanesulfonyl chloride, and the target product obtained by theprocess has high purity, reaction conditions are mild, the yield is high, the operation is simple and convenient, the production cost is low, and the suitability for amplifying production is achieved.

Synthesis process of amlodipine besylate

The invention discloses a synthesis process of amlodipine besylate, relates to the technical field of medicine synthesis and solves the problems of low product purity and poor product quality controllability of products prepared by the existing synthesis process. According to the synthesis process, phthalic anhydride is used as raw materials; the parameters of the synthesis process are controlled;the technical flow process is shortened; the synthesis cost is reduced; the product yield is as high as 91 percent; the purity of the prepared amlodipine besylate is as high as 99.5 percent. The self-made amlodipine besylate are used as raw materials for further preparing the amlodipine besylate tablets; the product cost is reduced; the product quality controllability is high.

Delta-aminoalkylbenzofuranol ethers, and preparation method and application thereof

The invention relates to delta-aminoalkylbenzofuranol ethers represented by chemical structural formula I shown in the description, and an application thereof in the preparation of herbicides. In thechemical structural formula I, R is selected from C1-C2 alkyl groups, and n is selected from 2, 3 and 4.

Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.

Synthesis technology of amlodipine maleate

The invention discloses a synthesis technology of amlodipine maleate and relates to the technical field of medicine synthesis, aiming at solving the problem in an existing synthesis technology that more byproducts and impurities exist in industrial production. By controlling parameters of the synthesis technology and reducing the content of the impurities, the purity of the prepared amlodipine maleate reaches 99.5 percent; the self-made amlodipine maleate is used as a raw material for further preparing the amlodipine maleate, so that the cost of a product is reduced and the quality controllability of the product is strong.