N-(4-ethynylphenyl)-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-(4-ethynylphenyl)-4-methylbenzenesulfonamide
• CAS No.: 190908-70-4
• Molecular Formula: C₁₅H₁₃NO₂S
• Molecular Weight: 271.34
• Mol file: 190908-70-4.mol

Synonyms:N-(4-ethynylphenyl)-4-methylbenzenesulfonamide

Chemical Property of N-(4-ethynylphenyl)-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-ethynylphenyl)-4-methylbenzenesulfonamide

There total 2 articles about N-(4-ethynylphenyl)-4-methylbenzenesulfonamide 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: 99.0%

N-tosyl-4-iodoaniline (158268-30-5) + trimethylsilylacetylene (1066-54-2) → N-(4-ethynylphenyl)-4-methylbenzenesulfonamide (190908-70-4)

Guidance literature:

N-tosyl-4-iodoaniline; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere; Sealed tube;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Sealed tube;

DOI:10.1039/C6OB02602H

Reference yield: 91.0%

4-Ethynylaniline (14235-81-5) + p-toluenesulfonyl chloride (98-59-9) → N-(4-ethynylphenyl)-4-methylbenzenesulfonamide (190908-70-4)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.8b00410

Reference yield: 95.0%

N-(4-ethynylphenyl)-4-methylbenzenesulfonamide (190908-70-4) + methyl (5-phenylpent-1-en-3-yl) carbonate (376647-56-2) → (S)-4-methyl-N-(4-(3-phenethylpent-4-en-1-yn-1-yl)phenyl)benzenesulfonamide

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tetrakis(acetonitrile)copper(I)tetrafluoroborate; C₃₅H₄₃N₂O₃P; In acetonitrile; at 20 - 60 ℃; for 24h; enantioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.0c08283

upstream raw materials:

4-Ethynylaniline

p-toluenesulfonyl chloride

N-tosyl-4-iodoaniline

trimethylsilylacetylene

Refernces

• 1、 Thirupataiah,Mounika, Guntipally,Reddy, Gangireddy Sujeevan,Kumar, Jetta Sandeep,Hossain, Kazi Amirul,Medishetti, Raghavender,Samarpita, Snigdha,Rasool, Mahaboobkhan,Mudgal, Jayesh,Mathew, Jessy E.,Shenoy, Gautham G.,Rao, C. Mallikarjuna,Chatti, Kiranam,Parsa, Kishore V.L.,Pal, Manojit. "PdCl2-catalyzed synthesis of a new class of isocoumarin derivatives containing aminosulfonyl / aminocarboxamide moiety: First identification of a isocoumarin based PDE4 inhibitor". supporting information. . Retrieved 2021/05/17.
• 2、 Malpani, Yashwardhan R.,Biswas, Bishyajit Kumar,Han, Hong Sik,Jung, Young-Sik,Han, Soo Bong. "Multicomponent Oxidative Trifluoromethylation of Alkynes with Photoredox Catalysis: Synthesis of α-Trifluoromethyl Ketones". supporting information. p. 1693 - 1697. Retrieved 2018/04/16.