1-[(2S)-2-[(7-Chlorobenzo[b]thien-3-yl)Methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-IMidazole

Base Information

• Chemical Name: 1-[(2S)-2-[(7-Chlorobenzo[b]thien-3-yl)Methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-IMidazole
• CAS No.: 583057-51-6
• Molecular Formula: C₂₀H₁₅Cl₃N₂OS
• Molecular Weight: 437.777
• Mol file: 583057-51-6.mol

Synonyms:(S)-Sertaconazole;1-[(2S)-2-[(7-Chlorobenzo[b]thien-3-yl)Methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-IMidazole

Chemical Property of 1-[(2S)-2-[(7-Chlorobenzo[b]thien-3-yl)Methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-IMidazole

Chemical Property:

• Boiling Point: 614.1±55.0 °C(Predicted)
• PKA: 6.68±0.12(Predicted)
• PSA: 55.29000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 7.01610

Purity/Quality:

98% ^*data from raw suppliers

(S)-Sertaconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (S)-Sertaconazole is the (S)-enantiomer of Sertaconazole, an imidazole antifungal agent that inhibits the synthesis of ergosterol, an essential cell wall component of fungi.

Technology Process of 1-[(2S)-2-[(7-Chlorobenzo[b]thien-3-yl)Methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-IMidazole

There total 10 articles about 1-[(2S)-2-[(7-Chlorobenzo[b]thien-3-yl)Methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-IMidazole 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: 82.0%

7-chloro-3-(chloromethyl)benzo[b]thiophene + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → sertaconazole (99592-32-2,583057-51-6,583057-48-1)

Guidance literature:

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol; With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In water; toluene; at 50 ℃; for 0.25h; Inert atmosphere;

7-chloro-3-(chloromethyl)benzo[b]thiophene; In water; toluene; at 50 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jacs.0c03197

Reference yield:

3-Bromomethyl-7-chlorobenzothiophene (17512-61-7) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → sertaconazole (99592-32-2,583057-51-6,583057-48-1)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) HMPT, RT; 2.) HMPT, 50 deg C, 1 h, 3.) HMPT, 0 deg C, 5 h;;

Reference yield:

C6H4ClIS → sertaconazole (99592-32-2,583057-51-6,583057-48-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: [Au₂(μ-bis(diphenylphosphino)methane)₂](OTf)₂; sodium carbonate / acetonitrile / 15 h / Inert atmosphere; Irradiation; Glovebox

3.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Cooling with ice

5.1: tetra-(n-butyl)ammonium iodide; sodium hydroxide / toluene; water / 0.25 h / 50 °C / Inert atmosphere

5.2: 4 h / 50 °C / Inert atmosphere

With potassium tert-butylate; [Au₂(μ-bis(diphenylphosphino)methane)₂](OTf)₂; tetra-(n-butyl)ammonium iodide; sodium carbonate; potassium carbonate; methanesulfonyl chloride; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jacs.0c03197

upstream raw materials:

3-Bromomethyl-7-chlorobenzothiophene

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

2-chloro-6-iodoaniline

(7-chlorobenzo[b]thiophen-3-yl)methanol

Refernces

• 1、 Abdel-Megied, Ahmed M.,Hanafi, Rasha S.,Aboul-Enein, Hassan Y.. "A chiral enantioseparation generic strategy for anti-Alzheimer and antifungal drugs by short end injection capillary electrophoresis using an experimental design approach". . p. 165 - 176. Retrieved 2017/11/27.
• 2、 -. "METHOD FOR MANUFACTURING IMIDAZOLE COMPOUNDS AND SALTS AND PSEUDOPOLYMORPHS THEREOF". Page/Page column 6. . Retrieved 2008/06/13.