5-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide

Base Information

• Chemical Name: 5-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide
• CAS No.: 16673-34-0
• Molecular Formula: C16H17ClN2O4S
• Molecular Weight: 368.841
• Hs Code.: 2935909550
• European Community (EC) Number: 240-722-5
• UNII: 8TF6P2NUB5
• DSSTox Substance ID: DTXSID1057660
• Nikkaji Number: J318.290H
• Wikidata: Q72453005
• ChEMBL ID: CHEMBL3188223
• Mol file: 16673-34-0.mol

Synonyms:5-chloro-2-methoxy-N-(2-(4-sulfamoylphenyl)ethyl)benzamide

Chemical Property of 5-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide

Chemical Property:

• Appearance/Colour: Light yellow solid
• Melting Point: 209-214 °C
• Refractive Index: 1.597
• PKA: 10.14±0.10(Predicted)
• PSA: 106.87000
• Density: 1.357 g/cm³
• LogP: 4.14050
• Storage Temp.: Refrigerator
• Solubility.: Soluble in DMSO (up to 45 mg/ml).
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 368.0597559
• Heavy Atom Count: 24
• Complexity: 515

Purity/Quality:

99% ^*data from raw suppliers

4-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzeneSulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23-24-25
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N
• Description: NLRP3i (16673-34-0) is an NLRP3 inflammasome inhibitor which likely acts via interfering with the formation of the NLRP3 inflammasome complex and which exhibits promising?in vivo?protective activities in mouse acute myocardial infarction models. It blocks ASC aggregation, blocks the release of IL-1β and the activation of caspase-1 in macrophages expressing constitutively active NLRP3 but does not directly inhibit caspase-1.1,2?Limits infarct size after myocardial ischemia-reperfusion as well as leukocyte infiltration in a peritonitis model in mice.2

Technology Process of 5-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide

There total 16 articles about 5-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

C15H11ClO5 + 4-(2-aminoethyl)benzenesulfonamide (35303-76-5) → 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide (16673-34-0)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/chem.202103196

Reference yield: 74.0%

5-chloro-2-methoxybenzoic acid (3438-16-2) + 4-(2-aminoethyl)benzenesulfonamide (35303-76-5) → 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide (16673-34-0)

Guidance literature:

With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20 ℃; for 1h; Milling;

DOI:10.1039/c3cc47905f

Reference yield: 68.0%

4-(2-[(5-chloro-2-methoxyphenyl)formamido]ethyl)benzene-1-sulfonyl chloride (33924-54-8) → 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide (16673-34-0)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 120 ℃; for 0.166667h; Sealed tube; Cooling with ice;

DOI:10.1021/acs.joc.6b02242

upstream raw materials:

phthalic anhydride

Glibenclamid

4-[4-(β-{2-methoxy-5-chlorobenzamido}-ethyl)benzenesulfonyl]-1.1-pentamethylene-semicarbazide

2-methoxy-5-chlorobenzoyl chloride

Downstream raw materials:

C₂₅H₂₈ClN₃O₅S

Ethyl 4-<2-(5-chloro-2-methoxybenzamido)ethyl>benzenesulfonamidecarbamate

N-{4-[N-(2-bromobenzylcarbamoyl)sulfamoyl]-phenethyl}-5-chloro-2-methoxybenzamide

Glibenclamid

Refernces

• 1、 Sanz, Dionisia,Claramunt, Rosa M.,Alkorta, Ibon,Sanchez-Sanz, Goar,Elguero, Jose. "The structure of glibenclamide in the solid state". . p. 246 - 255. Retrieved 2012.
• 2、 -. "Synthesis method of glibenclamide". Paragraph 0051. . Retrieved 2018/04/26.
• 3、 -. "Synthetic process of 4-[2-(5-chloro-2-methoxy benzamide)ethyl]benzsulfamide". . . Retrieved 2016/11/14.