539-03-7

Usage

Uses

Used in Pharmaceutical Preparations:
4'-Chloroacetanilide is utilized in the pharmaceutical industry as an essential component in the preparation of various medications. It is particularly used with a PGC (Porous Graphitized Carbon) column, which is a chromatographic technique employed to separate and analyze different components in a mixture.
Used in the Synthesis of Alprazolam:
In the field of medicinal chemistry, 4'-chloroacetanilide serves as a crucial intermediate in the synthesis of alprazolam, a widely prescribed medication for the treatment of anxiety and panic disorders. 4'-CHLOROACETANILIDE plays a vital role in the chemical reactions that lead to the formation of the final drug product.

Purification Methods

Crystallise the anilide from EtOH or aqueous EtOH. [Beilstein 12 IV 1178.]

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 60-29-7 diethyl ether 
• 45964-97-4 1-(4-chlorophenyl)guanidine 
• 56-23-5 tetrachloromethane 
• 579-11-3 N-chloroacetanilide 
• 128-09-6 N-chloro-succinimide 
• 103-84-4 Acetanilid 
• 108-86-1 bromobenzene 
• 64-17-5 ethanol 
• 67-66-3 chloroform 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 15386-78-4 N-(4-chlorophenyl)malonamic acid 
• 63581-16-8 N-dichloroiodanyl-acetanilide 
• 860574-47-6 N-acetyl-N'-allyl-N-(4-chloro-phenyl)-thiourea 

Downstream Products

• 3027-00-7 4-chloro-diacetanilide 
• 10416-61-2 N-(4-Chlorphenyl)-N-(trimethylsilyl)-acetamid 
• 129276-16-0 4-chloro-3-(phthalimidomethyl)acetanilide 
• 129276-15-9 4-chloro-2-(phthalimidomethyl)acetanilide 
• 128799-88-2 N-(p-Chlorobenzoyl)-N-acetyl-p-chloroaniline 
• 79043-95-1 N-[4-Chloro-2-((E)-3-oxo-but-1-enyl)-phenyl]-acetamide 
• 30649-58-2 2,3,4,6-Tetra-O-acetyl-1<(acetyl)(4-chlorphenyl)amino>-1-desoxy-β-D-glucopyranose 
• 22459-83-2 N-(3-bromo-4-chlorophenyl)acetamide 
• 73568-41-9 2,6-dichloroquinoline-3-carbaldehyde 
• 881-51-6 N-(4-chloro-2-nitrophenyl)-acetamide 
• 88-43-7 4-chloroaniline-3-sulfonic acid 
• 89894-27-9 N-(4-chloro-2,6-dinitrophenyl)acetamide 
• 133-74-4 2-amino-5-chlorobenzenesulfonic acid 
• 385843-42-5 N-allyl-N-(4-chloro-phenyl)acetamide 

Relevant academic research and scientific papers

Transamidation and Decarbonylation of N-Phthaloyl-Amino Acid Amides Enabled by Palladium-Catalyzed Selective C–N Bond Cleavage

Amides are important functional synthons that have been widely used in the construction of peptides, natural products, and drugs. The C–N bond cleavage provides the direct method for amide conversion. However, amides, especially secondary amides, tend to

Preparation method of acetamide compound

The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.

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.

Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino) Acetate (ortho-NosylOXY)-Mediated Double Beckmann Rearrangement of Ketoximes under Microwave Irradiation: A Mechanistic Perception

A method for Beckmann rearrangement using ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino) acetate (o-NosylOXY) under microwave irradiation is reported. Ketoximes (19 examples) are converted to the corresponding amides/lactams with 69–97% yields in ～10 minutes without any Lewis acid or co-catalyst. This is an example of halogen-free organocatalytic Beckmann rearrangement. Nuclear magnetic resonance (NMR)- and high-resolution mass spectrometry (HRMS)-based detailed mechanistic investigation suggest that o-NosylOXY acts as an initiator. Such initiators are reported before based on density functional theory (DFT) calculations. However, we report here the HRMS signatures of two transient intermediates, the nitrilium ion and the nitrilium ion's dimeric species. Rigorous NMR-based investigation of the reaction mechanism is performed. Our results indicate that the reported Beckmann rearrangement proceeds via two consecutive rearrangements. (Figure presented.).

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water

Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.