{3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-aziridinyl}(phenyl)methanone

Base Information

• Chemical Name: {3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-aziridinyl}(phenyl)methanone
• CAS No.: 825603-52-9
• Molecular Formula: C₂₂H₁₈ClNO₃S
• Molecular Weight: 411.909
• Mol file: 825603-52-9.mol

Synonyms:

Chemical Property of {3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-aziridinyl}(phenyl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-aziridinyl}(phenyl)methanone

There total 5 articles about {3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-aziridinyl}(phenyl)methanone 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: 54.0%

N,N-dichloro-p-toluenesulfonamide (473-34-7) + (2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one (22966-11-6) → {3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]aziridin-2-yl}(phenyl)methanone (825603-52-9)

Guidance literature:

With 4 A molecular sieve; copper(I) triflate; In acetonitrile; at 0 ℃; for 10h;

DOI:10.1055/s-2004-831203

Reference yield:

2-Mercaptobenzothiazole (149-30-4,118090-09-8) + {3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]aziridin-2-yl}(phenyl)methanone (825603-52-9) → N-((1S,2R)-1-(benzo[d]thiazol-2-ylthio)-1-(2-chlorophenyl)-3-oxo-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide + N-((1R,2S)-1-(benzo[d]thiazol-2-ylthio)-1-(2-chlorophenyl)-3-oxo-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide + (2S,3R)-2-benzoyl-3-(2-chlorophenyl)-1-(p-toluenesulfonyl)aziridine (825603-52-9)

Guidance literature:

{3-(2-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]aziridin-2-yl}(phenyl)methanone; With C₇₀H₉₆LaN₈O₈⁽³⁺⁾*3CF₃O₃S^(1-); In 1,2-dichloro-ethane; at 35 ℃; for 0.166667h; Resolution of racemate;

2-Mercaptobenzothiazole; In 1,2-dichloro-ethane; at 35 ℃; for 3h; enantioselective reaction; Resolution of racemate;

DOI:10.1021/acs.orglett.9b02058

Reference yield:

(2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one (22966-11-6) + [N-(p-tolylsulfonyl)imino]phenyliodinane (55962-05-5) → (2S,3R)-2-benzoyl-3-(2-chlorophenyl)-1-(p-toluenesulfonyl)aziridine (825603-52-9) + (2R,3S)-2-benzoyl-3-(2-chlorophenyl)-1-(p-toluenesulfonyl)aziridine (825603-52-9)

Guidance literature:

(2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one; With copper(I) triflate; (S,S)-1,8-bis[4-(1-methylethyl)oxazolin-2-yl]-anthracene; In dichloromethane; at 24 ℃; for 1h;

[N-(p-tolylsulfonyl)imino]phenyliodinane; In dichloromethane; at 24 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1039/b404134h

upstream raw materials:

N,N-dichloro-p-toluenesulfonamide

(2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one

1-(2-chloro-phenyl)-3-phenyl-2-propen-1-one

toluene-4-sulfonamide

Refernces

• 1、 Xu, Jiaxi,Ma, Linge,Jiao, Peng. "Asymmetric aziridination of chalcones catalyzed by a novel backbone 1,8-bisoxazolinylanthracene (AnBOX)-copper complex". . p. 1616 - 1617. Retrieved 2004.
• 2、 Chen, Dianjun,Timmons, Cody,Guo, Li,Xu, Xin,Li, Guigen. "One-pot stereoselective synthesis of anti 3-alkyl and 3-aryl-N-p-tosyl- aziridine-2-ketones and 3-aryl-N-p-tosyl-aziridine-2-carboxylates". . p. 2479 - 2484. Retrieved 2007/10/03.