6833-13-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzanilide is utilized as an intermediate in the synthesis of various pharmaceuticals. Its role in the creation of drugs is vital, given its chemical properties that facilitate its integration into medicinal compounds.
Used in Dye Industry:
In the dye industry, 2-Chlorobenzanilide is employed as an intermediate for the production of different dyes. Its chemical structure allows it to contribute to the formation of colorants used in various applications.
Used in Enzyme Research:
2-Chlorobenzanilide is used as a substrate in the study of the enzyme arylamine N-acetyltransferase. This application is crucial for understanding the enzyme's function in drug metabolism, potentially leading to advancements in how drugs are processed within the body.

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

Upstream product

• 71225-69-9 (2-chlorophenyl)phenylmethanone oxime 
• 71225-69-9 (Z)-N-[(2-chlorophenyl)(phenyl)methylidene]hydroxylamine 
• 609-65-4 o-chlorobenzoyl chloride 
• 62-53-3 aniline 
• 21122-36-1 2-Chlor-thiobenzoesaeure-S-phenylester 
• 118-91-2 ortho-chlorobenzoic acid 
• 587-14-4 N,N'-diphenylsulfamide 
• 694-59-7 pyridine N-oxide 
• 59387-00-7 2-Chlor-N-phenylbenzimidchlorid 
• 110-05-4 di-tert-butyl peroxide 
• 108-90-7 chlorobenzene 
• 103-70-8 Formanilid 
• 103-71-9 phenyl isocyanate 
• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 

Downstream Products

• 109806-80-6 N-phenyl-2-(phenylthio)benzamide 
• 59387-00-7 2-Chlor-N-phenylbenzimidchlorid 
• 319-39-1 N-(p-chlorophenyl)-o-chlorobenzamide 
• 55501-45-6 2-chloro-N-(4-nitrophenyl)benzamide 
• 70132-85-3 2-chloro-4'-diethylamino-benzophenone 
• 5892-87-5 (2-Chloro-benzoyl)-phenyl-carbamic acid 2-chloro-1-methyl-ethyl ester 
• 5866-84-2 (2-Chloro-benzoyl)-phenyl-carbamic acid allyl ester 
• 146516-68-9 6-chloro-2-trimethylsilyl-benzanilide 
• 136146-81-1 3-Amino-4-(4-fluoro-phenyl)-2-phenyl-2H-isoquinolin-1-one 
• 93-98-1 N-phenyl benzoyl amide 
• 1015-89-0 6(5H)-phenanthridinone 
• 22978-30-9 N-phenyl-o-chlorothiobenzamide 
• 146516-75-8 7-chloro-3-(4'-methoxyphenyl)-phthalide 
• 146516-81-6 7-chloro-3-hydroxy-2-phenyl-2,3-dihydro-1H-isoindol-1-one 

Relevant academic research and scientific papers

Synthesis of Aza[ n]phenacenes (n = 4-6) via Photocyclodehydrochlorination of 2-Chloro- N-aryl-1-naphthamides

A novel methodology for the synthesis of aza[n]phenacenes was successfully developed utilizing photocyclodehydrochlorination reaction of 2-chloro-N-aryl-1-naphthamides. In these key intermediates, the factors influencing the photoreaction were studied. The target aza[n]phenacenes were obtained by triflation or chlorination from prepared phenanthridinones, followed by hydrogenation. The introduction of a nitrogen atom into a phenacene skeleton induced changes in the physicochemical properties. The important properties of prepared aza[n]phenacenes (n = 4-6) were studied experimentally and by density functional theory calculations and were compared to those of their carbo analogues. Furthermore, some important features of the crystalline aza[n]phenacenes were investigated, including intermolecular interaction in the crystal lattice and the increased solubility or decreased melting points.

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.

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.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Method for synthesizing amide compound through photocatalysis in water phase

The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.

AGRICULTURAL CHEMICALS

The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

The use of Cr (CO)6 as an alternative CO source in Pd-catalyzed C-N bond formation: Synthesis of benzamides

An efficient strategy for the synthesis of benzamides from acetamides and aryl iodides using 1?mol% Pd (OAc)2 as catalyst and Cr (CO)6 as CO-precursor is described. This new synthetic methodology displays high functional group tolerance on both substrates and avoids the need for ligands, reducing agents, or other additives. The corresponding products were obtained in good to excellent yields at atmospheric pressure under mild reaction conditions.

Metal-Free Sustainable Synthesis of Amides via Oxidative Amidation Using Graphene Oxide as Carbocatalyst in Aqueous Medium

Abstract: We describe an efficient, clean and metal-free procedure for the synthesis of amides via oxidative amidation of aldehydes with anilines using graphene oxide (GO) as a recyclable catalyst and KBrO3 as a mild oxidant in aqueous medium under microwave irradiation. GO nanosheets were prepared and characterized by XRD, TEM, SEM, and FT-IR, analyses. GO showed high compatibility with KBrO3 in water and offered high TOF value (1.30 × 10?3 mol?g?1 min?1). GO oxygen functionalities catalyze the oxidative amidation effectively in mild condition with high recyclability. A plausible mechanism was proposed by the isolating the intermediate. Graphic Abstract: [Figure not available: see fulltext. ]