33924-54-8

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(2-(5-CHLORO-2-METHOXY BENZAMIDO)ETHYL)BENZENESULFONYL CHLORIDE is used as a reagent for the synthesis of pharmaceutical compounds due to its ability to alter the molecular structure, which is essential in creating new drugs with improved efficacy and safety profiles.
Used in Agrochemical Production:
In the agrochemical industry, 4-(2-(5-CHLORO-2-METHOXY BENZAMIDO)ETHYL)BENZENESULFONYL CHLORIDE is utilized as a reagent for the synthesis of agrochemicals, contributing to the development of more effective and safer products for agricultural applications.
Used in Dye and Pigment Manufacturing:
4-(2-(5-CHOLRO-2-METHOXY BENZAMIDO)ETHYL)BENZENESULFONYL CHLORIDE is also used in the manufacturing of dyes and pigments, where its unique chemical properties contribute to the creation of specialty chemicals with specific color and stability characteristics.
Used in Specialty Chemicals Production:
4-(2-(5-CHLORO-2-METHOXY BENZAMIDO)ETHYL)BENZENESULFONYL CHLORIDE finds application in the production of specialty chemicals, where its reactivity and structural modification capabilities are harnessed to produce chemicals with tailored properties for specific industrial uses.
Safety Considerations:
It is important to handle 4-(2-(5-CHLORO-2-METHOXY BENZAMIDO)ETHYL)BENZENESULFONYL CHLORIDE with care due to its corrosive and toxic nature, which can cause severe skin and eye irritation. Proper safety measures and personal protective equipment are essential when working with 4-(2-(5-CHOLRO-2-METHOXY BENZAMIDO)ETHYL)BENZENESULFONYL CHLORIDE.

InChI:InChI=1/C16H15Cl2NO4S/c1-23-15-7-4-12(17)10-14(15)16(20)19-9-8-11-2-5-13(6-3-11)24(18,21)22/h2-7,10H,8-9H2,1H3,(H,19,20)

Upstream product

• 16673-34-0 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 33924-49-1 DK₁₃ 
• 64-04-0 phenethylamine 
• 3438-16-2 5-chloro-2-methoxybenzoic acid 

Downstream Products

• 16673-34-0 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide 
• 33924-53-7 4-[2-(5-Chloro-2-methoxy-benzoylamino)-ethyl]-benzenesulfonic acid 
• 10238-21-8 Glibenclamid 

Relevant academic research and scientific papers

Intermolecular C-H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

An atom- and step-economic intermolecular multi-component palladium-catalyzed C-H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho -directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Pd-catalyzed amidation of 1,3-diketones with CO and azidesviaa nitrene intermediate

An efficient Pd-catalyzed amidation of 1,3-diketones has been developed using carbon monoxide and organic azides. This reaction provides a step-economic approach to produce β-ketoamides from readily available compounds under mild ligand-, oxidant-, and base-free conditions. The mechanistic studies showed that the reaction occurred through anin situgenerated isocyanate intermediate.

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

Intermolecular C?H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates

Amide bond formation is one of the most important reactions in organic chemistry because of the widespread presence of amides in pharmaceuticals and biologically active compounds. Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium-catalyzed three-component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene-intermediates and direct C?H functionalization. Notably, the reaction proceeds in an intermolecular fashion with N2 as the only by-product, and either directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh-nitrene intermediate.

N-HYDROXY-BENZENE-SULFONAMIDE DERIVATIVES AND THEIR USES THEREOF

Inhibitors with anti-inflammatory agents are provided, as are methods of using the analogs to inhibit inflammation and prevent or treat diseases and conditions associated with inflammation, such as multiple sclerosis and autoinflammatory diseases.

Structural Insights of Benzenesulfonamide Analogues as NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization

NLRP3 inflammasome plays critical roles in a variety of human diseases and represents a promising drug target. In this study, we established the in vivo functional activities of JC124, a previously identified NLRP3 inflammasome inhibitor from our group, in mouse models of Alzheimer's disease and acute myocardial infarction. To understand the chemical space of this lead structure, a series of analogues were designed, synthesized, and biologically characterized. The results revealed the critical roles of the two substituents on the benzamide moiety of JC124. On the other hand, modifications on the sulfonamide moiety of JC124 are well tolerated. Two new lead compounds, 14 and 17, were identified with improved inhibitory potency (IC50 values of 0.55 ± 0.091 and 0.42 ± 0.080 μM, respectively). Further characterization confirmed their selectivity and in vivo target engagement. Collectively, the results strongly encourage further development of more potent analogues based on this chemical scaffold.

Development and Characterization of a Hydroxyl-Sulfonamide Analogue, 5-Chloro-N-[2-(4-hydroxysulfamoyl-phenyl)-ethyl]-2-methoxy-benzamide, as a Novel NLRP3 Inflammasome Inhibitor for Potential Treatment of Multiple Sclerosis

In our efforts to develop novel small-molecule inhibitors for the NOD-like receptor family pyrin-domain-containing 3 (NLRP3) inflammasome as potential disease-modifying agents to treat neurological disorders including multiple sclerosis (MS), a hydroxyl sulfonamide analogue JC-171 has been rationally designed and biologically characterized both in vitro and in vivo. Our studies established that JC-171 dose dependently inhibited LPS/ATP-induced interleukin-1β (IL-1β) release from J774A.1 macrophages with an IC50 of 8.45 ± 1.56 μM. Selective inhibition of the NLRP3 inflammasome induced IL-1β release by this compound was also confirmed using mouse bone-marrow-derived macrophages and LPS-challenged mice in vivo. Furthermore, immunoprecipitation study revealed that JC-171 interfered with NLRP3/ASC interaction induced by LPS/ATP stimulation. More importantly, JC-171 treatment delayed the progression and reduced the severity of experimental autoimmune encephalomyelitis (EAE), a mouse model of MS, in both prophylactic and therapeutic settings. This coincided with blocking of IL-1β production and a pathogenic Th17 response. Collectively, these results suggest that JC-171 is a selective NLRP3 inflammasome inhibitor with biological activity in vivo, thus strongly encouraging further development of this lead compound as a potential therapeutic agent for human MS.

Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides

A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.

Synthetic process of 4-[2-(5-chloro-2-methoxy benzamide)ethyl]benzsulfamide

The invention discloses a synthetic process of 4-[2-(5-chloro-2-methoxy benzamide)ethyl]benzsulfamide, and belongs to the technical field of medicinal synthesis processes. According to the process, 5-chloro-2-methoxybenzoic acid and phenylethylamine serve as the raw materials, and a target product is obtained through reactions of four steps including acylating chlorination, amidation, chlor amidation osulfonation and sulfanil amination. By means of the synthesis method, low-price industrial chemicals serve as raw materials and reaction reagents, single-solvent systems are adopted, smooth process connection is achieved, reaction yield is increased, process operation is simplified, and production cost is reduced while raw material cost is reduced.

Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis

A newly designed robust and safe laboratory scale reactor for syntheses under sealed-vessel conditions at 250 °C maximum temperature and 20 bar maximum pressure is presented. The reactor employs conductive heating of a sealed glass vessel via a stainless steel heating jacket and implements both online temperature and pressure monitoring in addition to magnetic stirring. Reactions are performed in 10 mL borosilicate vials that are sealed with a silicone cap and Teflon septum and allow syntheses to be performed on a 2-6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device and a standard microwave reactor suggest that results obtained using microwave conditions can be readily mimicked in the operationally much simpler and smaller conventionally heated device.