N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal

Base Information

• Chemical Name: N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal
• CAS No.: 103790-08-5
• Molecular Formula: C₁₅H₁₇NO₄S
• Molecular Weight: 307.37
• Mol file: 103790-08-5.mol

Synonyms:N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal

Chemical Property of N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal

There total 6 articles about N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal 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: 93.0%

methanol (67-56-1) + N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide (1150-26-1) → N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal (103790-08-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; at 2 - 20 ℃; for 0.133333h; Temperature;

Reference yield: 77.0%

N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide (1150-26-1) → N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal (103790-08-5)

Guidance literature:

In methanol; Ambient temperature; anodic oxidation, graphite felt anode, platinum cathode, one compartment cell, tetraethylammonium perchlorate;

Reference yield:

methanol (67-56-1) + phenyl toluenesulfonamide (68-34-8) → N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal (103790-08-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0037-1610317

upstream raw materials:

N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide

methanol

4-methoxy-aniline

p-toluenesulfonyl chloride

Downstream raw materials:

N-(2-chloro-4-methoxyphenyl)-4-methylbenzenesulfonamide

4-methyl-N-(1-methyl-4-oxocyclohexa-2,5-dien-1-yl)benzenesulfonamide

Refernces

• 1、 Kondo, Masaru,Wathsala,Sako, Makoto,Hanatani, Yutaro,Ishikawa, Kazunori,Hara, Satoshi,Takaai, Takayuki,Washio, Takashi,Takizawa, Shinobu,Sasai, Hiroaki. "Exploration of flow reaction conditions using machine-learning for enantioselective organocatalyzed Rauhut-Currier and [3+2] annulation sequence". . p. 1259 - 1262. Retrieved 2020.
• 2、 Carreno, M. Carmen,Ribagorda, Maria. "Anodic oxidation of N-protected 4-methoxy anilines: Improved synthesis of quinone imine acetals". . p. 1231 - 1234. Retrieved 2000.
• 3、 More, Satish G.,Kamble, Rohit B.,Suryavanshi, Gurunath. "Oxidative Radical-Mediated Addition of Ethers to Quinone Imine Ketals: An Access to Hemiaminals". . p. 2107 - 2116. Retrieved 2021.
• 4、 Chen, Xingyu,Lu, Sixian,Deng, Ping,Chang, Xiaoqiang,Zhao, Yifan,Ma, Yue,Zhang, Dong,Xia, Fei,Yang, Lan,Wang, Jigang,Sun, Peng. "Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans". . p. 94 - 102. Retrieved 2021/10/05.