Reaction Of Chloroacetyl Chloride Research Articles

Synthesis of new N-Substituted -3- chloro -2- azetidinones for 2, 4-Diamino-6-phenyl-1,3,5-triazine

The current study involved synthesis of several new N-Substituted -
 3- chloro -2- azetidinones for 2,4-Diamino-6-phenyl-1,3,5-triazine by two
 steps. The first step includes preparation of Schiff bases (Al-A6) by
 condensation of 2,4-Diamino-6-pheny]-1,3,5-triazine with many substituted
 aldehydes, then the second step includes preparation new six azetidinone
 compounds (B1-B6) by reaction of chloro acetyl chloride with the
 prepared Schiff bases in first step. The prepared compounds were
 characterized by physical properties, FT-IR, UV and some of them by 'H-
 NMR, "C-NMR spectroscopy were recorded.

Synthesis of N-Substituted 3-Chloro- 2-azetidinones for 2, 4-diamino-6- hydroxy pyrimidin

This search involved synthesis of several new N-Substituted -3-chloro-
 2-azetidinones which were known as a high medicinal effectiveness for 2,
 4-Diamino-6-hydroxy pyrimidin in two steps. The first step included
 preparation Shiff bases (1-6) by condensation of 2, 4-Diamino-6-hydroxy
 pyrimidin with many substituted aldehydes(4-hydroxy benzaldehyde, 2-
 bromobenzaldehyde, 4-dimethyl amino benzaldehyde, = 4-nitro
 benzaldehyde, salicylaldehyde, 4-chlorobenzaldehyde), then the second
 step included, preparation new six azetidinones compounds (7-12) by
 reaction of chloroacetylchloride with the prepared Schiff bases in the first
 step in the presence of triethylamine. The structures of synthesized
 compounds were- characterized by physical properties (FT-IR, UV and
 some of them by 'H-NMR, C_NMR spectroscopy) were recorded.

Synthesis, characterization and antimicrobial activity of some new N-substituted-oxindole derivatives

The aim of this research is the synthesis of new heterocyclic derivatives containing 4-oxo-thiazolidines, tetrazol or oxoazetidin ring from oxindole. To obtain these derivatives, oxindole [1] was chosen as the starting material to synthesize -chloro-N-oxindole acetamide [2] which was prepared by two methods. The first method by direct condensation of oxindole with chloroacetylchloride in presence of triethylamine and absolute ethanol as solvent. The second method by reaction of chloroacetylchloride with sodium salt of oxindole. Treatment of -chloro-N-oxindole acetamide [2] with hydrazine hydrate gave -hydrazino-N-(oxindole)acetamide [3] which is the desired chiron. Compound [3] was reacted with different aromatic aldehydes which gave the corresponding Schiff base derivatives [4a-d]. 4-Oxothiazolidines [5a-d], tetrazole [6a-d] and 2-oxoazetidine [7a-d], were obtained from cyclization of Schiff base derivatives [4a-d] using mercaptoacetic acid, sodium azide and chloroacetylchloride respectively. The synthesized compounds were characterized by spectral methods FTIR, 1H-NMR,and 13C-NMR . Biological activities of prepared compounds were tested against three types of bacteria, which showed promising antibacterial activity of 4-oxothiazolidines [5a, b] and tetrazole [6b].

Synthesis, characterization, and evaluation of the biological activity of tetrazole compounds derived from the nitrogenous base uracil

This research included synthesis of heterocyclic compounds, in the first step where the compound [M1] was prepared from the reaction of chloroacetyl chloride with the nitrogenous base uracil using a basic medium. Compound [M1] then were converted into compound [M2] by reacted with hydrazine hydrate (95%) in absolute ethanol using sodium hydroxide (KOH). Schiff bases [M3-M9] were prepared from the reaction of the compound [M2] prepared in the second step with some substitutes of benzaldehyde in absolute ethanol. Tetrazole derivatives [M10-M16] were prepared from the reaction of Schiff bases [M9-M3] with sodium azide in tetrahydrofuran(THF) as a solvent. After purifying the product, the synthetic compounds were diagnosed with some spectral methods such as [UV], [FTIR], [1H NMR] and [13C-{1H}NMR], in addition to determining the melting and purity levels of the prepared compounds and monitoring the progress of the reactions using TLC thin layer chromatography. The effect of some prepared compounds on the growth of two types of bacterial isolates, known to be resistant to antibiotics, one negative for Gram stain [Gr-ve], which is Pseudomonas aeruginosa, and the second positive for Gram stain [Gr + ve], which is Staphylococcus aurous, were used antibiotics Amoxicillin and Ampicillin. Some of the prepared compounds showed high inhibitory efficacy against the used bacteria in addition, the conformation of prepared compounds at the lower energy level were studied.

Synthesis and Pharmacological Evaluation of 2-(4-(3 (Substituted Phenyl) Acryloyl) Phenoxy)-N, N Diphenylacetamides

Recently a series of Schiff bases of diphenylamine derivatives have been synthesized and evaluated in vitro for their antibacterial activity against pathogenic both Gram-positive bacteria B. subtitles and Gram-negative bacteria E. coli using ciprofloxacin as standard drug at conc. of 50 μg/ml and 100 μg/ml. Literature review revels that chalcones possesses various biological activities like antimicrobial, antiviral, anti-inflammatory, anticancer and sedative etc. Therefore the present study was designed on synthesis and pharmacological evaluation of 2-(4-(3 (Substituted Phenyl) Acryloyl) Phenoxy)-N, N Diphenylacetamides. Target compound was synthesized by reaction of chloroacetylchloride with diphenylamine to afford 2-chloro-N, N-diphenylacetamide which further by reaction with substituted Chalcones and characterized following recrystallization and evaluated for anti-microbial potential through cup-diffusion method. In results, the target compounds were tested for activity against B. Subtilis, E.Coli and C. albicans. The chalcones having the lipophilic 4-chloro group (RKCT2) showed the greatest antimicrobial activity (zone of inhibition 20 & 22 mm against. B. subtilis, E. Coli, C. Albicans respectively. It suggests further researchers to go through anti-microbial evaluations against a more varieties of bacteria and fungi.
 Keywords: Schiff bases of diphenylamine derivatives, antibacterial activity, Gram-positive bacteria, 2-(4-(3 (Substituted Phenyl) Acryloyl) Phenoxy)-N, N Diphenylacetamides

Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide

The title compound, C13H14O2N3Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P21/c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) A, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N–H···O and C–H···O interactions, the former interactions result in the formation of dimers corresponding to R 2 2 (10) graphset motif and the dimers are further connected by C–H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λmax = 298 nm was determined by UV-Vis spectrophotometer.

Synthesis of 3-(aminooxoethyl)-6-methyl-1-(thiethan-3-yl)-pyrimidine-2,4-(1H,3H)-diones

A new approach to prepare 2-chloroacetamides has been developed, based on the reaction of chloroacetyl chloride with excess of secondary amines. Alkylation of 6-methyl-1-(thiethan-3-yl)pyrimidine- 2,4(1H,3H)-dione with the synthesized 2-chloroacetamides in the presence of potassium carbonate has afforded N 3 -acetamido-substituted 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-diones.

Synthesis of Some new 2-(4-Aryliminophenoxy)N-Arylacetamide Via p-hydroxy benzaldehyde.

Chloroacetamide derivatives (2a-g) have been prepared through reaction of chloroacetyl chloride(1) (which prepared by the reaction of chloroacetic acid with thionyl chloride) with primary aromatic amines and sulfa compounds to afford compounds (2a-g) which then reacted with p-hydroxy benzaldehyde via Williamson reaction to obtaine the new compounds 2-(4-formyl phenoxy)-N-aryl acetamide (3a-g). Finally , compounds (3a-g) will be use as a good synthon to prepare the Schiff bases represented by compounds 2-(4-aryliminophenoxy)-N-arylacetamide (4a-g). through , reaction with some primary aromatic amine. All the prepared compounds were investigated by the available physical and spectroscopic methods.

Synthesis of Some new 2-(4-Aryliminophenoxy)N-Arylacetamide Via p-hydroxy benzaldehyde.

Chloroacetamide derivatives (2a-g) have been prepared through reaction of chloroacetyl chloride(1) (which prepared by the reaction of chloroacetic acid with thionyl chloride) with primary aromatic amines and sulfa compounds to afford compounds (2a-g) which then reacted with p-hydroxy benzaldehyde via Williamson reaction to obtaine the new compounds 2-(4-formyl phenoxy)-N-aryl acetamide (3a-g). Finally , compounds (3a-g) will be use as a good synthon to prepare the Schiff bases represented by compounds 2-(4-aryliminophenoxy)-N-arylacetamide (4a-g). through , reaction with some primary aromatic amine. All the prepared compounds were investigated by the available physical and spectroscopic methods.

Synthesis of Novel Azetidinyl-3-(isonicotinamide-yl)-6-iodoquinazolin- 4-ones as Antimicrobial and Antitubercular Agents

A novel new series of 2-[(4'-oxo-3'-chloro-2'-phenylazetidin-1'-yl)-aminomethyl]-3-[N-isonicotinamide-yl]-6-iodo-quinazolin-4-ones were synthesized using the reaction of chloroacetylchloride and appropriate Schiff base. The synthesized compounds were characterized on the basis of their elemental and spectral analysis (IR, 1H-NMR, 13C-NMR and mass spectrometry). All newly synthesized compounds were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv. They were also tested in vitro for antibacterial activity against selected human pathogens such as E. coli, P. aeruginosa, K. pneumoniae, S. typhi, S. aureus, S. pyogenus, B. subtilis and antifungal activity against C. albicans, A. niger, A. clavatus strains. The selected 6-iodo-quinazolinonones showed promising biological activity and could be useful as antimicrobial agents. 

Ultrasound promoted clay catalyzed efficient and one pot synthesis of substituted oxindoles

A simple facile, one-pot synthesis of oxindoles in reasonable purity is reported via intramolecular Friedal–Craft cyclization. Clay KSF is an inexpensive, efficient and mild catalyst for the synthesis of substituted oxindoles by the reaction of chloroacetyl chloride and various anilines under the influence of ultrasonic irradiation under solvent-free conditions. The remarkable advantages of this method are the simple experimental procedures, short reaction times, high yields of products, suitability for a wide variety of substituents, and the green aspects through the avoidance of toxic catalyst and solvents.

Synthesis, characterization and extraction studies of N,N″-bis[1-biphenyl-2-hydroxyimino-2-(4-acetylanilino)-1-ethylidene]-diamines and their homo-and heteronuclear copper(II) complexes

A new series of homo- and heteropolynuclear copper(II) complexes of N,N″-bis[1-biphenyl-2-hydroxyimino-2-(4-acetylanilino)-1-ethylidene]-diamines have been prepared and characterized by different physical techniques. The starting point of the research was the reaction of chloroacetyl chloride with biphenyl in the presence of aluminum chloride. 4-Biphenylhydroximoyl chloride was obtained by reacting synthesized 4-(chloroacetyl)biphenyl with alkyl nitrite. Substituted 4-(alkylaminoisonitrosoacetyl) biphenyl (ketooxime) was prepared by reacting 4-biphenylhydroximoyl chloride with 4-aminoacetophenone in EtOH. Homodi-, homotrinuclear and heterodinuclear copper(II) perchlorate complexes of tetradentate Schiff bases which possess N4 donor sets derived from the condensation of 4-(arylaminoisonitrosoacetyl)biphenyl and diamine derivatives were synthesized and characterized. Elemental analysis, FT-IR, ESR, molar conductivity, magnetic moment measurements and thermal analyses studies were utilized for the investigation of the complexes. The free ligands were also characterized by 1H- and 13C-NMR spectra. Elemental analyses, stoichiometric and spectroscopic data of the metal complexes indicated that the metal:ligand ratio of dinuclear copper(II) complexes were found to be 2: 1 while this ratio was 3: 2 in trinuclear copper(II) complexes and the metal complexes indicated that the metal ions are coordinated to the oxime and imine nitrogen atoms. The extraction abilities of the novel ligands were also evaluated in chloroform by using several transition metal picrates such as Mn2+, Co2+, Ni2+, Cu2+, Zn2+, Pb2+, Cd2+, Hg2+. It has been observed that both ligands show a high affinity to Cu2+ ions.

Unusual reaction of chloroacetyl chloride with 1,2-dichloroethene. Synthesis and properties of 2-chlorovinyl dichloromethyl ketone

The reaction of chloroacetyl chloride with 1,2-dichloroethene in the presence of AlCl3 unexpectedly led to the formation of (E)-1,1,4-trichlorobut-3-en-2-one whose structure was proved by 1H and 13C NMR, IR, and mass spectra and independent synthesis. A probable reaction scheme was proposed, which involves transformation of initially formed 1,2,4-trichloro-3-oxobutan-2-yl cation by the action of AlCl3. The high reactivity of the vinylic halogen atom in (E)-1,1,4-trichlorobut-3-en-2-one was demonstrated by its reactions with nitrogen-centered nucleophiles (triethylamine, aniline, 3,5-dimethyl-1H-pyrazole) and sodium sulfide. These reactions involved only the C-Cl bond in the vinyl fragment and afforded (4,4-dichloro-3-oxobut-2-en-1-yl)triethylammonium chloride, 1,1-dichloro-4-phenylaminobut-3-en-2-one, 1-(4,4-dichloro-3-oxobut-2-en-1-yl)-3,5-dimethyl-1H-pyrazole, and 4,4′-thiobis(1,1-dichlorobut-3-en-2-one), respectively. The reaction of 1,1,4-trichlorobut-3-en-2-one with benzylhydrazine gave a mixture of 1,3- and 1,5-disubstituted pyrazoles.

Investigation of the Reaction of Chloroacetyl Chloride with 1,5-Benzothiazepines: Selective Synthesis of Azeto[2,1-d][1,5]benzothiazepines by Green Chemical Methods and Their Biological Activity

An efficient and exclusive synthesis of the tricyclic azeto[2,1-d][1,5]benzothiazepine ring system has been developed. By use of microwave irradiation in the presence of basic alumina, the reaction time has been brought down from hours to minutes with improved yields in comparison to conventional heating. Antimicrobial screening of the synthesized compounds has shown promising activity.

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NOVEL 2,3-DISUBSTITUTED QUINAZOLIN4(3H)ONES

3-Amino-2-(substituted phenoxymethyl / propyl) quinazolin4(3H)ones 4a-c have been prepared. Refluxing 4 with 5-nitro-2furaldehyde / 4-nitrobenzaldehyde afforded the corresponding substituted methylidene-amino derivatives 5 and 6 respectively. Reaction of 4 with isatin yielded the indolylideneamino derivatives 7. Refluxing 4 with ofloxacin acid chloride furnished the corresponding carboxamides 8. Reaction of chloroacetyl chloride with 4c produced the 3-chloroacetylamino derivative 9 which upon further reaction with the potassium salts of some antibacterial acids gave the corresponding carboxylate derivatives 10. Sixteen compounds were screened for their antibacterial and antifungal activities. Thirteen compounds were found to possess (high to moderate) activity against Pseudomonas aerugenosa and some of them were also active against Escherichia coli. Only one compound was found to exhibit moderate antifungal activity against Candida albicans.

Synthesis and Characterization of Novel Methacrylate Monomers Having Pendant Oxime Esters and Their Copolymerization with Styrene

New methacrylate monomers, 2‐{[(diphenylmethylene)amino]oxy}‐2‐oxoethyl methacrylate (DPOMA) and 2‐{[(1‐phenylethylidene)ami no]oxy}‐2‐oxoethyl methacrylate (MMOMA) were prepared by reaction of sodium methacrylate with diphenylmethanone O‐(2‐chloroacetyl) oxime and 1‐phenylethanone O‐(2‐chloroacetyl) oxime, respectively. They were obtained from a reaction of chloroacetyl chloride with benzophenone oxime or acetophenone oxime. The free‐radical‐initiated copolymerization of (DPOMA) and (MMOMA) with styrene (St) were carried out in 1,4‐dioxane solution at 65°C using 2,2‐azobisisobutyronitrile (AIBN) as an initiator with different monomer‐to‐monomer ratios in the feed. The monomers and copolymers were characterized by FTIR, 1H‐ and 13C‐NMR spectral studies. The copolymer compositions were evaluated by nitrogen content in polymers. The reactivity ratios of the monomers were determined by the application of Fineman–Ross and Kelen–Tüdös methods. The molecular weights (M¯w and M¯n) and polydispersity index of the polymers were determined by using gel permeation chromatography. Thermogravimetric analysis of the polymers reveals that the thermal stability of the copolymers increases with an increase in the mole fraction of St in the copolymers. The activation energies of the thermal degradation of the polymers were calculated with the MHRK method. Glass transition temperatures of the copolymers were found to decrease with an increase in the mole fraction of DPOMA or MMOMA in the copolymers. The antibacterial and antifungal effects of the monomers and polymers were also investigated on various bacteria and fungi. The photochemical properties of the polymers were investigated by UV and FTIR spectra.

Design, synthesis and in vitro antibacterial studies of some biologically significant N-3-chloro-4-[2' -hydroxy-5' -(phenylazo)phenyl]azetidin-2-ones

The title compounds 3a-h were prepared via the reaction of imine derivatives viz. substituted 2-hydroxy-5-(4'-nitrophenylazo)benzylidine anilines 2a-h with ketenes generated by the reaction of chloroacetylchloride with triethylamine in 1,4-dioxane. The structures of synthesized compounds were assigned by elemental analysis and IR and 1 H NMR spectral datas. All the synthesized azetidin-2-ones 3a-h were assayed for their in vitro antibacterial activity against several Gram-positive and Gram-negative bacterial pathogens. Some of the compounds have shown marginal activity.

Synthesis and characterization of new ketooximes and their complexes

The starting point of the research was the reaction of chloroacetyl chloride with biphenyl in the presence of aluminum chloride. 4-Biphenylhydroximoyl chloride (HL) was obtained by reacting synthesized 4-(chloroacetyl)biphenyl with alkyl nitride. Four new substituted 4-(alkylaminoisonitrosoacetyl)biphenyles (ketooximes) were prepared by reacting 4-biphenylhydroximoyl chloride with corresponding amines in EtOH. The following amines were used for ligands: p-toluidine, p-chloroaniline, pyrrolidine, and 4-aminoacetophenone. Mononuclear complexes with a metal-ligand ratio of 1: 2 were prepared using cadmium(II), cobalt(II), copper(II), nickel(II), lead(II), and zinc(II) salts. These compounds have been characterized by elemental analyses, AAS, infrared spectra and magnetic susceptibility measurements. The ligands have been further characterized by 1H NMR. The results suggest that the ketooximes act as bidentate ligands which bond metal ions through the oxime and carbonyl oxygen.

Preparation and Root Growth‐Inhibitory Activity of N‐Substituted 2‐(2‐Chloroacetamido)‐3‐(furan‐2‐yl)propanamides.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Preparation and Root Growth-Inhibitory Activity of N-Substituted 2-(2-Chloroacetamido)-3-(furan-2-yl)propanamides

A series of N-substituted 2-(2-chloroacetamido)-3-(furan-2-yl)propanamides (16--18) was prepared through the reaction of chloroacetyl chloride with N-substituted 2-amino-3-(furan-2-yl)propanamides (15), which were obtained via condensation of 2-(tert-butoxycarbonylamido)-3-(furan-2-yl)propanoic acid (Boc-furylalanine) (8) with amines (9, 11, 13), followed by hydrolysis of the resultant N-substituted Boc-furylalanine acid amides (10, 12, 14) in the presence of HCl/dioxane. The biological activity of the prepared 16, 17 and 18 as root growth inhibitors was examined by germination assay using rape seed. At the concentration of 5.0 x10 (-5) M, the most active compound, 2-(2-chloroacetamido)-N-(2,6-diethylphenyl)-3-(furan-2-yl)propanamide (16 n), showed potent root growth-inhibitory activity of 76% towards rape seedlings.