39086-61-8

Usage

Uses

Used in Organic Synthesis:
2-chloro-N-ethylacetanilide is used as a key intermediate in the synthesis of various organic compounds, contributing to the formation of complex molecules that are essential in the development of new chemical entities.
Used in Dye Production:
In the dye industry, 2-chloro-N-ethylacetanilide is used as a precursor for the production of dyes, which are then incorporated into textiles, plastics, and other materials to impart color and enhance their visual appeal.
Used in Pharmaceutical Industry:
2-chloro-N-ethylacetanilide is used as a building block in the development of pharmaceutical compounds, playing a crucial role in the synthesis of drugs that target various medical conditions. Its reactivity and structural features make it a valuable component in the creation of novel therapeutic agents.
Used in Chemistry Research:
In academic and industrial research settings, 2-chloro-N-ethylacetanilide is used as a model compound to study chemical reactions and mechanisms, providing insights into the behavior of similar compounds and advancing the understanding of chemical processes.

InChI:InChI=1/C10H12ClNO/c1-2-12(10(13)8-11)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

Upstream product

• 103-69-5 N-ethyl-N-phenylamine 
• 79-04-9 chloroacetyl chloride 
• 4348-19-0 N-ethylaniline hydrochloride 
• 79-11-8 chloroacetic acid 

Downstream Products

• 861797-52-6 2-(bis[(ethyl-phenyl-carbamoyl)-methyl]-amino)-N-ethyl-N-phenyl-acetamide 
• 61-28-9 1-ethyl-1,3-dihydro-2H-indol-2-one 
• 107348-02-7 Diethyl-dithiocarbamic acid (ethyl-phenyl-carbamoyl)-methyl ester 
• 99275-60-2 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-N-ethyl-N-phenyl-acetamide 
• 120508-35-2 2-Chloro-N-ethyl-N-phenyl-thioacetamide 
• 66325-67-5 diethyl (2-(ethyl(phenyl)amino)-2-oxoethyl)phosphonate 
• 1243284-06-1 2-[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]-N-ethyl-N-phenylacetamide 
• 529-65-7 N-ethylacetanilide 
• 103-69-5 N-ethyl-N-phenylamine 
• 226952-92-7 6-chloro-N-ethyl-8,9-dihydro-9-methyl-8-oxo-2-phenyl-N-phenyl-7H-purin-7-acetamide 
• 99275-66-8 4-Hydroxy-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl-phenyl-amide 
• 103148-97-6 N-Ethyl-2-(triphenylphosphoranyliden)acetanilid 
• 103149-04-8 N-Ethyl-2,3-butadienanilid 
• 921601-16-3 3,3,7,7-tetra[N-ethyl-N-phenyl(acetamide)-2-oxymethyl]-5-oxanonane 

Relevant academic research and scientific papers

Palladium-catalyzed olefination of aryl/alkyl halides with trimethylsilyldiazomethane via carbene migratory insertion

The direct olefination of aryl/alkyl halides with trimethylsilyldiazomethane (TMSD) as a C1- or C2-unit was achieved successfully via a metal carbene migratory insertion process, which offered a new access to afford (E)-vinyl silanes and (E)-silyl-substituted α,β-unsaturated amides in good yields and high chemoselectivity.

Synthesis and structure-activity relationships of LP1 derivatives: N-methyl-N-phenylethylamino analogues as novel MOR agonists

The opioid pharmacological profile of cis-(-)-N-normetazocine derivatives is deeply affected by the nature of their N-substituents. Here, our efforts were focused on the synthesis and pharmacological evaluation of novel derivatives of the lead LP1, a multitarget opioid analgesic compound featuring an N-phenylpropanamido substituent. LP1 derivatives 5a-d and 6a-d were characterized by flexible groups at the N-substituent that allow them to reposition themselves relative to cis-(-)-N-normetazocine nucleus, thus producing different pharmacological profiles at the mu, delta and kappa opioid receptors (MOR, DOR and KOR) in in vitro and in vivo assays. Among the series, compound 5c, with the best in vitro and in vivo profile, resulted a MOR agonist which displays a KiMOR of 6.1 nM in a competitive binding assay, and an IC50 value of 11.5 nM and an Imax of 72% in measurement of cAMP accumulation in HEK293 cells stably expressing MOR, with a slight lower efficacy than LP1. Moreover, in a mouse model of acute thermal nociception, compound 5c, intraperitoneally administered, exhibits naloxone-reversed antinociceptive properties with an ED50 of 4.33 mg/kg. These results expand our understanding of the importance of N-substituent structural variations in the opioid receptor profile of cis-(-)-N-normetazocine derivatives and identify a new MOR agonist useful for the development of novel opioid analgesics for pain treatment.

Anti-proliferative activity, molecular modeling studies and interaction with calf thymus DNA of novel ciprofloxacin analogues

Abstract: In our pursuit to expand new potential anticancer leads, a series of eighteen novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized and evaluated anti-proliferative activity against five human cancer cell lines such as A549 (lung cancer), Mia Paca (pancreatic cancer), HeLa (cervical cancer), MDA MB-231 (breast cancer), MCF-7 (breast cancer) and normal embryonic kidney?cell line (HEK) were carried out using MTT assay. Few of the synthesized analogues exhibited potent anticancer activity against the cancer cell lines at a lower concentration. The synthesized compounds showed the less toxic effect on normal human embryonic kidney?cell line (HEK) compared with doxorubicin. Noticeably, compound 3o exhibited potent activity against all five cancer cell lines compared with ciprofloxacin. Further study exposed that compound 3o could competently intercalate into calf thymus DNA to form 3o-DNA complex which might block DNA replication to apply anti-proliferative activity. Docking simulation studies supported by molecular interactions with DNA type II topoisomerase. These derivates can become lead structures for the development of potential anticancer drugs. Graphical Abstract: Eighteen CP analogues were synthesized and evaluated for anti-proliferative activity. The interactions with DNA topoisomerase II were supported by molecular docking studies. 3o showed promising anticancer activity than CP against MCF7 cell line and interaction with calf thymus DNA was studied by fluorescence spectroscopy.[Figure not available: see fulltext.].

Derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative

We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of a-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel a-imino carboxylic acid derivatives such as a-imino phenyl ester, perfluoroalkyl etsers, imides, and thioester. The asymmetric Mannich reaction of those novel imine derivatives with 1,3-dicarbonyl compound is also described, and the novel a-imino imide gave improved chemical yield and stereoselectivity compared with those obtained by the use of the conventional a-imino ester-type substrate.

Electrochemical reduction of 2-chloro-N-phenylacetamides at carbon and silver cathodes in dimethylformamide

Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the direct electrochemical reduction of 2-chloro-N-methyl-N-phenylacetamide (1a), 2-chloro-N-ethyl-N-phenylacetamide (1b), and 2-chloro-N-phenylacetamide (1c) at carbon and silver cathodes, as well as the catalytic reduction of these compounds by electrogenerated nickel(I) salen, in dimethylformamide (DMF) containing 0.050 M tetramethylammonium tetrafluoroborate (TMABF4). Cyclic voltammograms for reduction of 1a and 1b show a single irreversible cathodic peak for cleavage of the carbon-chlorine bond, but two irreversible cathodic peaks are observed in cyclic voltammograms for reduction of 1c. Controlled-potential reduction of 1a and 1b gives mixtures of dechlorinated amide and N-alkyl-N-phenylaniline, whereas bulk electrolyses of 1c afford N-phenylacetamide in almost quantitative yield. In addition, bulk electrolyses of 1a and 1b result in the formation of very small amounts of dimeric species that arise from coupling of the radical intermediate formed by one-electron cleavage of the carbon-chlorine bond. On the basis of the coulometric n values and product distributions, together with computations based on density functional theory, we propose mechanistic pictures for the reduction of 1a and 1b that involve radical intermediates, whereas reduction of 1c involves carbanion intermediates.

Evaluation of N-substitution in 6,7-benzomorphan compounds

6,7-Benzomorphan derivatives, exhibiting different μ, δ, and κ receptor selectivity profiles depending on the N-substituent, represent a useful skeleton for the synthesis of new and better analgesic agents. In this work, an aromatic ring and/or alkyl residues have been used with an N-propanamide or N-acetamide spacer for the synthesis of a new series of 5,9-dimethyl-2′-hydroxy-6,7-benzomorphan derivatives (12-22). Data obtained by competition binding assays showed that the μ opioid receptor seems to prefer an interaction with the 6,7-benzomorphan ligands having an N-substituent with a propanamide spacer and less hindered amide. Highly stringent features are required for δ receptor interaction, while an N-acetamide spacer and/or bulkier amide could preferentially lead to κ receptor selectivity. In the propanamide series, compound 12 (named LP1) displayed high μ affinity (Ki = 0.83 nM), good δ affinity (Ki = 29 nM) and low affinity for the κ receptor (Ki = 110 nM), with a selectivity ratio δ/μ and κ/μ of 35.1 and 132.5, respectively. Further, in the adenylyl cyclase assay, LP1 displayed a μ/δ agonist profile, with IC50 values of 4.8 and 12 nM at the μ and δ receptors, respectively. The antinociceptive potency of LP1 in the tail-flick test after sc administration in rat was comparable with the potency of morphine (ED50 = 2.03 and 2.7 mg/kg, respectively), and was totally reversed by naloxone. LP1, possessing a μ/δ agonist profile, could represent a lead in further developing benzomorphan-based ligands with potent in vivo analgesic activity and a reduced tendency to induce side effects.

Switching high two-photon efficiency: From 3,8,13-substituted triindole derivatives to their 2,7,12-isomers

Bridging the triindole core and triarylboryl acceptor by an ethenylene linker at the 3,8,13- or 2,7,12-position, the resultant 3-BET and 2-BET show two-photon absorption (TPA) cross sections of δ = 2100 and 2500 GM (at 810 nm by femtosecond pulses in THF), respectively. The TPA enhancement of the 2,7,12-isomers is also found when comparing 3-BYT and 2-BYT (δ = 870 and 1900 GM) and 3-NET and 2-NET (36 and 400 GM).

Synthesis and antimicrobial activities of some imidazole substituted indoles

The compounds 1-substituted 2-(imidazol-1-yl)-3-(4,5-diarylimidazol-2-yl) indoles 2, 1-substituted 2-(imidazol-1-yl)-3-(phenanthro[9,10-d]imidazol-2-yl) indoles 3 and 1-substituted 2-(imidazol-1-yl)-3-(benzimidazol-2-yl)indoles 4 have been synthesized from 1-substituted 2-(imidazol-1-yl)-3-formylindole 1. The structural elucidation of the synthesised compounds has been performed by IR, 1H NMR and mass spectroscopic data and elemental analyses. Antimicrobial activities of the compounds are examined and notable antifungal activity is obtained from some of the compounds as expected in comparison with the control agent ketoconazole.

Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization

A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright