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

Base Information

• Chemical Name: 4-methyl-N-(1-methyl-4-oxocyclohexa-2,5-dien-1-yl)benzenesulfonamide
• CAS No.: 1449770-03-9
• Molecular Formula: C₁₄H₁₅NO₃S
• Molecular Weight: 277.344
• Mol file: 1449770-03-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 4-methyl-N-(1-methyl-4-oxocyclohexa-2,5-dien-1-yl)benzenesulfonamide 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: 66.0%

methyllithium (917-54-4) + N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal (103790-08-5) → 4-methyl-N-(1-methyl-4-oxocyclohexa-2,5-dien-1-yl)benzenesulfonamide (1449770-03-9)

Guidance literature:

methyllithium; N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; water; Inert atmosphere;

DOI:10.1039/c3ob27491h

Reference yield: 58.0%

p-toluenesulfonyl chloride (98-59-9) + 4-amino-4-methylcyclohexa-2,5-dien-1-one → 4-methyl-N-(1-methyl-4-oxocyclohexa-2,5-dien-1-yl)benzenesulfonamide (1449770-03-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 23h;

DOI:10.1002/ejoc.201800962

Reference yield:

methyl bromide (74-83-9) + N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal (103790-08-5) → 4-methyl-N-(1-methyl-4-oxocyclohexa-2,5-dien-1-yl)benzenesulfonamide (1449770-03-9)

Guidance literature:

methyl bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

N-(p-toluenesulfonyl)-p-benzoquinone imine dimethyl acetal; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; hexane; water; for 10h;

DOI:10.1021/acs.orglett.7b01578

upstream raw materials:

methyllithium

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

p-toluenesulfonyl chloride

4-methoxy-aniline

Downstream raw materials:

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

Refernces

• 1、 Jia, Penghao,Zhang, Qinglong,Jin, Hongxing,Huang, You. "[3 + 2]-Annulation of Prop-2-ynylsulfonium Salts: Access to Hydroindol-5-ones Containing a Methylthio Group". . p. 412 - 415. Retrieved 2017.
• 2、 Wales, Steven. M.,Adcock, Holly V.,Lewis, William,Hamza, Daniel,Moody, Christopher J.. "Nitrogen-Bridged, Natural Product Like Octahydrobenzofurans and Octahydroindoles: Scope and Mechanism of Bridge-Forming Reductive Amination via Caged Heteroadamantanes". . p. 4696 - 4704. Retrieved 2018/09/14.