6974-10-3

Usage

Uses

Used in Organic Synthesis:
2-Ethoxycarbonyl-methyl-phthalimide is utilized as a reagent for the introduction of the 2-ethoxycarbonylmethyl group into a range of organic compounds. Its ability to facilitate such group incorporation is crucial for the synthesis of complex organic molecules, enhancing the diversity and functionality of chemical products.
Used in Pharmaceutical Production:
As an intermediate, 2-Ethoxycarbonyl-methyl-phthalimide plays a pivotal role in the manufacturing process of various pharmaceuticals. Its presence in the synthesis chain allows for the development of new drugs with potential therapeutic benefits, contributing to advancements in medicinal chemistry.
Used in Agrochemical Production:
Similarly, in the agrochemical industry, 2-Ethoxycarbonyl-methyl-phthalimide serves as an intermediate in the creation of compounds designed to protect crops and enhance agricultural productivity. Its involvement in the synthesis of agrochemicals underscores its importance in developing effective solutions for pest control and crop management.

Upstream product

• 38846-64-9 2-ethynylbenzaldehyde 
• 459-73-4 GlyOEt*HCl 
• 3842-20-4 N-(cyanomethyl)phthalimide 
• 141-78-6 ethyl acetate 
• 75-36-5 acetyl chloride 
• 101855-29-2 C₁₃H₁₁NO₄S₂ 
• 637-81-0 ethyl-2-azidoacetate 
• 85-44-9 phthalic anhydride 

Downstream Products

• 4743-52-6 N-(o-carboxybenzoyl)glycine 
• 99056-34-5 N-carbamoylmethyl-phthalamide 
• 1875-48-5 N-aminophthalamide 
• 75-00-3 chloroethane 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 56-40-6 glycine 
• 67429-32-7 2-Phthalimidomethyl-6-methyl-4-(4'-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 
• 13972-97-9 4-hydroxy-2-methyl-1(2H)-isoquinolone-3-carboxylic acid methyl ester 
• 477515-36-9 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(3,4,5-trimethoxybenzylidene)acetohydrazide 
• 477515-44-9 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide 
• 1345842-30-9 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-methylbenzylidene)acetohydrazide 
• 477515-24-5 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-hydroxybenzylidene)acetohydrazide 
• 477515-40-5 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-chlorobenzylidene)acetohydrazide 
• 1338229-70-1 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(2-nitrobenzylidene)acetohydrazide 

Relevant academic research and scientific papers

Methyl sulfonamide substituents improve the pharmacokinetic properties of bicyclic 2-pyridone based: Chlamydia trachomatis inhibitors

Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In vivo pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue 30 inhibited C. trachomatis infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg-1 showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. In vitro ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide 30, effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.

Reactant cum solvent water: Generation of transient λ3-hypervalent iodine, its reactivity, mechanism and broad application

An outstanding amidation/imidation process is demonstrated under metal-free benign reaction conditions by grafting terminal alkynes with varied amines and reactant cum solvent water. We explored diverse substrate scope in the nonconventional approach for synthesis of several classes of valuable compounds bearing amide linkages such as N-tosyl, N-aminotosyl, N-oxobenzyl, N-alkylated sugar-based secondary and tertiary chiral amides and also exploiting it for synthesis of valuable cyclic imides through simultaneous activation of triple bond and sp2C-H of aldehyde. The in situ-generated powerful reagent PhI(OH)2 enables selective cleavage and functionalization of terminal C-C triple bonds through simultaneous construction of C-N and C=O bonds. A measurable breakthrough in time-resolved ATR-MIR spectroscopy of the ongoing λ3-hypervalent iodine controlled reaction revealed formation of the unknown intermediates. The ATR-MIR technology is used for identifying infrared (IR) spectra of the individual intermediate/component present in the reaction mixture, which contains several compounds. The structures of the intermediates and their IR spectra were determined by DFT study. This unprecedented combination of experimental results and theoretical prediction provided useful information regarding the reaction insights such as the cleavage of triple bond, amination and amidation in the complex reaction process involving λ3-hypervalent iodine-bearing labile intermediates to the desired amide. The NMR and labelling (2H and 18O) studies supported the DFT-IR predicted reaction pathway.

An environmentally benign solvent/catalyst-free one-pot synthesis of N-substituted phthalimides via Aza-wittig reaction

For the first time an environmentally benign solvent/catalyst-free protocol for the synthesis of a variety of N-substituted phthalimides is submitted. It involves a one-pot coupling of nascent phosphazene generated in situ with phthalic anhydride. The protocol is novel in (1) avoiding toxic solvents, (2) no catalyst is employed and (3) no isophthalimide is formed as noted in the prevailing solution phase/catalysed methodology. Iranian Chemical Society 2012.

NEW SYNTHETIC "TRICKS". ONE-POT PREPARATION OF N-SUBSTITUTED PHTHALIMIDES FROM AZIDES AND PHTHALIC ANHYDRIDE

N-Substituted phthalimides can be obtained in very good yields, under essentially neutral conditions, by mixing or heating an alkyl (or aryl) azide, triphenylphosohine, and phthalic anhydride in benzene or toluene, in the presence of a catalytic amount of tetrabutylammonium cyanide.Application of the reaction into the domain of carbohydrates is promising.

Photochemical and Thermal Transformations of O-Alkyl-S-phthalylglycyl Xanthates

Phthalylglycyl chloride reacts with different potassium O-alkyl xanthates (alkyl = Et, n-Pr, i-Pr, n-Bu, i-Bu) around 0 deg C in ether solution to give the corresponding O-alkyl-S-phthalylglycyl xanthates (Ia-e).Irradiation of Ia-e in benzene with mercury lamp for 1-1.5 hr results in the formation of corresponding alkyl xanthates (Va-e) whereas thermal decomposition of Ia-e around 150-200 deg C for 20-30 min yields the corresponding esters (VIa-e) and carbon disulphide.