N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide

Base Information

• Chemical Name: N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide
• CAS No.: 141644-94-2
• Molecular Formula: C₃₁H₄₆N₂O₅S
• Molecular Weight: 558.783
• Mol file: 141644-94-2.mol

Synonyms:N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide

Chemical Property of N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide

There total 8 articles about N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide 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: 73.0%

N-(3-(4-bromophenoxy)propyl)-N-butylbutan-1-amine (627040-50-0) + N-(2-butyl-3-formylbenzofuran-5-yl)methanesulfonamide → N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide (141644-94-2)

Guidance literature:

N-(3-(4-bromophenoxy)propyl)-N-butylbutan-1-amine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

N-(2-butyl-3-formylbenzofuran-5-yl)methanesulfonamide; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.0c03197

Reference yield: 40.0%

N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide (437652-07-8) + 4-<3-(dibutylamino)propoxy>benzaldehyde (114980-27-7) → N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide (141644-94-2)

Guidance literature:

N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide; With n-butyllithium; In hexane; at 20 ℃; for 2h;

4-<3-(dibutylamino)propoxy>benzaldehyde; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Temperature; Time; Concentration;

Reference yield:

2-iodo-4-nitrophenol (89487-91-2) → N-(2-butyl-3-{[4-(3-dibutylaminopropoxy)-phenyl]-hydroxymethyl}-benzofuran-5-yl)-methanesulfonamide (141644-94-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

2.1: iron; ammonium chloride / ethanol; water / 1 h / 60 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere

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

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; di-isopropyl azodicarboxylate; [Au₂(μ-bis(diphenylphosphino)methane)₂](OTf)₂; iron; sodium carbonate; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jacs.0c03197

upstream raw materials:

1-chloro-3-(di-n-butylamino)-propane hydrochloride

4-hydroxy-benzaldehyde

N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide

4-<3-(dibutylamino)propoxy>benzaldehyde

Downstream raw materials:

dronedarone

2-n-butyl 3-[4-(3-di-n-butylamino-propoxy)benzyl] 5-methylsulfonamido benzofuran

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF DRONEDARONE BY OXIDATION OF A HYDROXYL GROUP". . . Retrieved 2013/09/12.