(E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide

Base Information

• Chemical Name: (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide
• CAS No.: 1426562-23-3
• Molecular Formula: C₂₅H₂₇NO₃
• Molecular Weight: 389.494
• Mol file: 1426562-23-3.mol

Synonyms:(E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide

Chemical Property of (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide

There total 4 articles about (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide 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:

N,N-diethyl 2-formyl-4,6-dimethoxybenzamide (868756-10-9) + (2-naphthalenylmethyl)triphenylphosphonium bromide (35160-95-3) → (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide (1426562-23-3) + (Z)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide (1426562-24-4)

Guidance literature:

(2-naphthalenylmethyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

N,N-diethyl 2-formyl-4,6-dimethoxybenzamide; In tetrahydrofuran; at 0 - 20 ℃; Overall yield = 68 %; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.01.074

Reference yield:

N,N-diethyl-2,4-dimethoxybenzamide (142601-55-6) → (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide (1426562-23-3) + (Z)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide (1426562-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

With N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; sec.-butyllithium; In tetrahydrofuran; cyclohexane; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;

DOI:10.1016/j.bmcl.2013.01.074

Reference yield:

2,4 dimethoxybenzoic acid (91-52-1) → (E)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide (1426562-23-3) + (Z)-N,N-diethyl-2,4-dimethoxy-6-(2-(naphthalen-2-yl)vinyl)benzamide (1426562-24-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride / 3 h / Inert atmosphere; Reflux

2.1: dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; sec.-butyllithium; In tetrahydrofuran; dichloromethane; cyclohexane; 4.1: |Wittig Olefination / 4.2: |Wittig Olefination;

DOI:10.1016/j.bmcl.2013.01.074

upstream raw materials:

N,N-diethyl-2,4-dimethoxybenzamide

N,N-diethyl 2-formyl-4,6-dimethoxybenzamide

(2-naphthalenylmethyl)triphenylphosphonium bromide

2,4 dimethoxybenzoic acid