6833-15-4

Usage

InChI:InChI=1/C13H10ClNO/c14-11-8-6-10(7-9-11)13(16)15-12-4-2-1-3-5-12/h1-9H,(H,15,16)

Upstream product

• 2998-98-3 (Z)-(4-chlorophenyl)(phenyl)methanone oxime 
• 104-88-1 4-chlorobenzaldehyde 
• 103-71-9 phenyl isocyanate 
• 108-90-7 chlorobenzene 
• 1871-38-1 phenyl 4-chlorobenzoate 
• 62-53-3 aniline 
• 28122-82-9 S-phenyl 4-chlorobenzothioate 
• 2362-79-0 N-(4-chlorobenzylidene)aniline 
• 75-05-8 acetonitrile 
• 77750-06-2 S-(4-methylphenyl) thio(4-chlorobenzoate) 
• 15163-60-7 p-chlorobenzoic acid potassium salt 
• 128100-67-4 1,2-bis(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)ethane-1,2-dione 
• 2998-98-3 4-cholorobenzophenone oxime 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 105702-86-1 4-chloro-4'-(N-methyl-anilino)-benzophenone 
• 37613-10-8 4-chloro-N-phenyl-benzimidoyl chloride 
• 129120-25-8 (4-chlorophenyl)(4-(dimethylamino)phenyl)methanone 
• 91790-87-3 N,N'-diphenyl-4-chlorobenzamidine 
• 5892-88-6 (4-Chloro-benzoyl)-phenyl-carbamic acid 2-chloro-1-methyl-ethyl ester 
• 5892-83-1 (4-Chloro-benzoyl)-phenyl-carbamic acid 2-methoxy-1-methyl-ethyl ester 
• 5892-74-0 (4-Chloro-benzoyl)-phenyl-carbamic acid isopropyl ester 
• 122399-73-9 3-<4-(4-chlorobenzoylamino)benzoyl>acrylic acid 
• 146516-80-5 5-chloro-3-(4'-methoxyphenyl)-phthalide 
• 60253-34-1 5-chloro-3-methylphthalide 
• 146516-89-4 2-Allyl-4-chloro-N-phenyl-benzamide 
• 146516-83-8 5-chloro-3-hydroxy-2-phenyl-2,3-dihydro-1H-isoindol-1-one 
• 146516-79-2 5-chloro-3-(2'-methoxyphenyl)-phthalide 
• 146516-71-4 2,N-dimethyl-4-chloro-benzanilide 

Relevant academic research and scientific papers

TBAI-catalyzed C–N bond formation through oxidative coupling of benzyl bromides with amines: a new avenue to the synthesis of amides

A new green approach for the synthesis of amide through TBAI-catalyzed oxidative coupling of benzyl bromides with amine was developed in the presence of tert-butyl hydroperoxide (TBHP) as an oxidant. Various electron-donating and withdrawing groups containing benzyl bromides and various amines, were subjected to the reaction and transformed to the corresponding amide in good to excellent yields.

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

A CO2-Catalyzed Transamidation Reaction

Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C-N Bond Cleavage

Palladium-catalyzed Hiyama coupling of active thioureas via selective C-N bond cleavage is reported. Notably, the new approach employed active thioureas as coupling partners in the presence of arylsilanes to give amides in good yield. Further, this strategy, which utilized CuF 2as a key oxidant and activator, afforded various amide products under mild conditions and an easy to handle procedure without extra base.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.