Synthesis of<i>N</i>-aryl 2-chloroacetamides and their chemical reactivity towards various types of nucleophiles

Abdel‐Latif, Ehab; Fahad, Mustafa M.; Ismail, Mohamed A.

doi:10.1080/00397911.2019.1692225

Cited by 17 publications

(7 citation statements)

References 49 publications

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“…A literature survey showed that the acetanilide derivatives 2a-f were obtained through acylation of the appropriate amines with chloroacetyl chloride using different reaction conditions such as triethylamine, potassium carbonate, sodium acetate or pyridine in different solvents such as glacial acetic acid, dichloromethane, DMF or acetone. [43][44][45][46] In this study, the acetanilide derivatives 2a-f were synthesized with good yield using acetic acid and sodium acetate according to the method by Kumar et al 47 On the other hand, intermediates 4a and b were synthesized by reacting 2-pyrrolidinone 3a or 2-piperidinone 3b with malononitrile in dry benzene via condensation reaction. 48 These intermediates were conrmed by their melting points, as reported.…”

Section: Chemistrymentioning

confidence: 99%

Pyrrolizine/indolizine-bearing (un)substituted isoindole moiety: design, synthesis, antiproliferative and MDR reversal activities, and in silico studies

AbdelSamad,

El-Saadi,

Gouda

et al. 2023

RSC Adv.

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Section: Chemistrymentioning

confidence: 99%

Pyrrolizine/indolizine-bearing (un)substituted isoindole moiety: design, synthesis, antiproliferative and MDR reversal activities, and in silico studies

AbdelSamad,

El-Saadi,

Gouda

et al. 2023

RSC Adv.

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“…The working electrode which represents alloy carbon steel with dimensions of (5 × 1.5 × 0.2) cm 3 , which represents the submerged part of the alloy. Platinum Auxiliary Electrode and Saturated Calomel Electrode (SCE) with a fiber-loggin capillary represent as a Reference Electrode (RE).…”

Section: The Potentiodynamic Polarization (Pdpmentioning

confidence: 99%

“…Many amide derivatives have been used as antifungals, antihistamines, worms, and antibacterial agents. For example, the compound N-aryl-2-chloroacetamides acts as an antimicrobial such as herbicides, antifungals, and disinfectants [3].…”

Section: ■ Introductionmentioning

confidence: 99%

Inhibition of Carbon Steel Corrosion by Some New Organic 2-Hydroselenoacetamide Derivatives in HCl Medium

Khalib¹,

Al-Hazam

Hassan

2022

Indones. J. Chem.

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This study aims to prepare 2-hydroselenoacetamide derivatives (5-8) to use some of these compounds as corrosion inhibition for carbon steel in 1 M HCl. The compound C10H10NO2Cl 1 was prepared by reacting between p-aminoacetophenone with chloroacetyl chloride, and then reacted 1 with substituted benzaldehyde to obtain the corresponding derivatives as C17H13N2O4Cl 2, C18H16NO4Cl 3 and C19H18NO4Cl 4. The last step in this study was conducted to obtain the organic hydroselenoacetamide such as C10H11NO2Se 5, C17H14N2O4Se 6, C18H17NO4Se 7, and C19H19NO4Se 8 by reacting chloroaminochalcone and sodium hydrogen selenide. All compounds were characterized by Fourier Transform Infrared Spectroscopy (FTIR), proton nuclear magnetic resonance (1H-NMR), and elemental analysis (CHN). The corrosion inhibition activity of C17H14N2O4Se 6, C18H17NO4Se 7 and C19H18NO4Cl 4 for carbon steel in 1 M HCl solution was investigated by using weight loss methods and electrochemical study. The activation energy of the corrosion reaction was also calculated. The effect of different concentrations and temperatures on inhibition efficiency was investigated. The results showed that the corrosion rate decreased with the increase of the concentration of inhibitors, while the inhibition efficiency and covered area decreased with an increase in the temperature. Polarization studies demonstrated that the inhibitors were of mixed type. The purpose of this study was to prepare, characterize and evaluate the corrosion inhibition activity of hydroselenide compounds for carbon steel in 1 M HCl.

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“…The same strategy for synthetic route of typical standard herbicides (acetochlor, metochlor and smetochlor) were used for the synthesis of chloroacetamide derivatives which based on the formation of Schiff base followed by chloroacetylation of imines (Abdel-Latif et al 2020).…”

Section: Synthesis Of Chloroacetamide Derivativesmentioning

confidence: 99%

Synthesis, Herbicidal Activity and Molecular Docking of some New Chloroacetamide Derivatives

El-Zemity

Esmaiel

Badawy

2021

Alexandria Science Exchange Journal

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Four novel chloroacetamide derivatives were synthesized 2-Chloro-N-(2,4-dichlorobenzyl)-N-(3,5dimethylphenyl)acetamide (2), 2-Chloro-N-(2,4dichlorobenzyl)-N-(2,5-dichlorophenyl)acetamide (4), 2-Chloro-N-cinnamyl-N-(4-sulfamoylphenyl)acetamide (6) and 2-chloro-N-(2,5-dichlorophenyl)-N-(2hydroxybenzyl)acetamide ( 8) and evaluated as herbicidal agents against two weed species; Anagallis arvensis as broad leaf weed and Lolium temulentum as a narrow weed in comparison with acetochlor as a standard herbicide. Mass spectra, 1 H-NMR and 13 C-NMR had approved the chemical structures of the synthesized compounds. Depending on the estimation of chlorophyll content, compounds 4 and 2 have been characterized as the most potent, against tested weeds and had EC50 values lower than acetochlor as standard herbicide. In addition, the molecular docking to the active sites of Very Long Chain Fatty Acid Synthase (VLCFAs) as a target enzyme shown that the derivatives gave minimal binding energy and acceptable affinity for the active site.

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Synthesis ofN-aryl 2-chloroacetamides and their chemical reactivity towards various types of nucleophiles

Cited by 17 publications

References 49 publications

Pyrrolizine/indolizine-bearing (un)substituted isoindole moiety: design, synthesis, antiproliferative and MDR reversal activities, and in silico studies

Pyrrolizine/indolizine-bearing (un)substituted isoindole moiety: design, synthesis, antiproliferative and MDR reversal activities, and in silico studies

Inhibition of Carbon Steel Corrosion by Some New Organic 2-Hydroselenoacetamide Derivatives in HCl Medium

Synthesis, Herbicidal Activity and Molecular Docking of some New Chloroacetamide Derivatives

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