6326-19-8

Usage

Uses

Used in Pharmaceutical Industry:
Felbamate Related Compound B (25 mg) (Phenethyl carbamate) is used as an impurity in the synthesis of Felbamate, an antiepileptic drug, for the treatment of seizures and epilepsy. Its structural similarity to meprobamate suggests that it may have potential applications in the development of new antiepileptic medications or as a reference compound in the study of drug interactions and mechanisms of action.

Upstream product

• 60-12-8 2-phenylethanol 
• 57913-41-4 2-phenylethyl chloroformate 
• 80639-71-0 2-phenylethyl azidocarbonate 
• 869111-28-4 N-(2-phenylethoxycarbonyl) hydroxylamine 
• 590-28-3 potassium cyanate 
• 917-61-3 sodium isocyanate 
• 143-33-9 sodium cyanide 
• 57-13-6 urea 

Downstream Products

• 74797-23-2 (5,11-Dihydro-10-thia-dibenzo[a,d]cyclohepten-5-yl)-carbamic acid phenethyl ester 
• 54957-93-6 C₉H₉Cl₂NO₂ 
• 4973-39-1 2-phenylethyl phenylcarbamate 
• 1280577-43-6 N-(cyclohex-2-enyl) phenethyl carbamate 
• 86217-38-1 4-phenyl-2-oxazolidinone 

Relevant academic research and scientific papers

ACETAMIDO-PHENYLBENZAMIDE DERIVATIVES AND METHODS OF USING THE SAME

The present disclosure relates to compounds of Formula (I): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for the treatment of disorders in which expression of P-glycoprotein and/or cytochrome P450 (e.g., CYP3A4) is modulated (e.g., cancers which have developed multi-drug resistance).

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

An efficient one-pot synthesis of industrially valuable primary organic carbamates and: N -substituted ureas by a reusable Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] using urea as a sustainable carbonylation source

An efficient synthesis of primary carbamates and N-substituted ureas is explored with a newly developed heterogeneous polymer supported iron catalyst in the presence of a sustainable carbonylation source. The Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] was synthesized by functionalization of Merrifield polymer followed by grafting of iron metal. The catalyst [FeII(Anthra-Merf)] was characterized by several techniques, like SEM, EDAX, TGA, PXRD, XPS, FTIR, CHN, AAS and UV-Vis analysis. The designed polymer embedded [FeII(Anthra-Merf)] complex is a remarkably successful catalyst for the synthesis of primary organic carbamates and N-substituted ureas by using safe carbonylation agent urea with different derivatives of alcohols and amines, respectively. The reported catalyst is a potential candidate towards contributing a satisfactory yield of isolated products under suitable reaction conditions. The catalyst is recyclable and almost non-leaching in nature after six runs with an insignificant drop in catalytic activity. Thus we found an economical and viable catalyst [FeII(Anthra-Merf)] for primary carbamates and N-substituted urea synthesis under moderate reaction conditions.

Triazinetriamine-derived porous organic polymer-supported copper nanoparticles (Cu-NPs@TzTa-POP): an efficient catalyst for the synthesis of: N -methylated products via CO2fixation and primary carbamates from alcohols and urea

In recent times, carbon dioxide fixation has received much attention for its potential application as an abundant C1 source and a range of important fine chemicals can be manufactured via this fixation. Here, a copper nanoparticle-decorated porous organic polymer-based (Cu-NPs@TzTa-POP) material was prepared by a simple in situ process. The catalyst was characterized by various techniques such as UV-vis spectra, FTIR spectra, HR-TEM, PXRD, N2 adsorption-desorption, TG-DTA, XPS, and AAS analysis. The synthesized heterogeneous catalyst showed excellent activity in an atmospheric carbon dioxide fixation reaction to produce N-methylated products from aromatic/heterocyclic amines in the presence of polymethyl-hydrosiloxane (PMHS) as the reducing agent at 80 °C within 12 h of the reaction. Through this catalytic N-methylation reaction, we obtained 98% yield of the product with turnover frequency ranging from 18 to 42 h-1. The catalyst is also very stable for the formation of primary carbamates from alcohols using the eco-friendly carbonylating agent, urea. Diverse alcohols (such as benzylic alcohols, phenols, heterocyclic alcohols, as well as aliphatic alcohols) showed much acceptance to this catalytic reaction and produced moderate to excellent yields of the respective carbamate products under ambient reaction conditions. Moreover, Cu-NPs@TzTa-POP is effortlessly recyclable and reusable without the extensive loss of active copper metal centres for many catalytic rounds (up to six catalytic rounds were examined).

An Fe3O4@SiO2/Schiff base/Cu(ii) complex as an efficient recyclable magnetic nanocatalyst for selective mono: N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids

An efficient, convenient and novel method for the selective mono N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids in the presence of a recyclable magnetic Cu(ii) nanocatalyst is described. A variety of mono N-arylated O-alkyl thiocarbamates and O-alkyl carbamates were prepared in good to excellent yields with a broad range of aryl coupling partners. The magnetic nanocatalyst can be easily recovered with an external magnetic field and reused at least five times without noticeable leaching or loss of its catalytic activity. This cost-effective and eco-friendly methodology has some other advantages, such as easy preparation of the catalyst, simple workup procedure, and easy purification, which makes this protocol interesting for the users in various fields of pharmacology and biotechnology systems.

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas

Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.

4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas

A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.

Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups

Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.

Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates

A novel class of 19 carbamates was synthesized, and their anticonvulsant activity was comparatively evaluated in the rat maximal electroshock (MES) and subcutaneous metrazol (scMet) seizure tests and pilocarpine-induced status epilepticus (SE) model. In spite of the alkyl-carbamates' close structural features, only compounds 34, 38, and 40 were active at the MES test. The analogues 2-ethyl-3-methyl-butyl-carbamate (34) and 2-ethyl-3-methyl-pentyl- carbamate (38) also exhibited potent activity in the pilocarpine-SE model 30 min postseizure onset. Extending the aliphatic side chains of homologous carbamates from 7 to 8 (34 to 35) and from 8 to 9 carbons in the homologues 38 and 43 decreased the activity in the pilocarpine-SE model from ED50 = 81 mg/kg (34) to 94 mg/kg (35) and from 96 mg/kg (38) to 114 mg/kg (43), respectively. The most potent carbamate, phenyl-ethyl-carbamate (47) (MES ED50 = 16 mg/kg) contains an aromatic moiety in its structure. Compounds 34, 38, 40, and 47 offer the optimal efficacy-safety profile and, consequently, are promising candidates for development as new antiepileptics.