(Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate

Base Information

• Chemical Name: (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate
• CAS No.: 1333419-42-3
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.338
• Mol file: 1333419-42-3.mol

Synonyms:(Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate

Chemical Property of (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate

There total 4 articles about (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate 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: 81.0%

(E)-methyl 3-(N-methylbenzamido)acrylate (1333419-27-4) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate (1333419-42-3)

Guidance literature:

With potassium hydrogen difluoride; oxygen; copper diacetate; palladium diacetate; potassium carbonate; CyJohnPhos; In acetic acid; tert-butyl alcohol; at 90 ℃; under 760.051 Torr; stereoselective reaction;

DOI:10.1002/anie.201101550

Reference yield:

N-methylbenzamide (88070-48-8) → (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate (1333419-42-3)

Guidance literature:

Multi-step reaction with 3 steps

1: titanium tetrachloride; triethylamine / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

2: benzene / 18 h / 80 °C

3: potassium hydrogen difluoride; oxygen; copper diacetate; palladium diacetate; potassium carbonate; CyJohnPhos / acetic acid; tert-butyl alcohol / 90 °C / 760.05 Torr

With potassium hydrogen difluoride; oxygen; copper diacetate; palladium diacetate; titanium tetrachloride; potassium carbonate; triethylamine; CyJohnPhos; In dichloromethane; acetic acid; tert-butyl alcohol; benzene; 3: Heck cross-coupling reaction;

DOI:10.1002/anie.201101550

Reference yield:

N-Formyl-N-methylbenzamide (141264-25-7) → (Z)-methyl 3-(N-methylbenzamido)-3-phenylacrylate (1333419-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 18 h / 80 °C

2: potassium hydrogen difluoride; oxygen; copper diacetate; palladium diacetate; potassium carbonate; CyJohnPhos / acetic acid; tert-butyl alcohol / 90 °C / 760.05 Torr

With potassium hydrogen difluoride; oxygen; copper diacetate; palladium diacetate; potassium carbonate; CyJohnPhos; In acetic acid; tert-butyl alcohol; benzene; 2: Heck cross-coupling reaction;

DOI:10.1002/anie.201101550

upstream raw materials:

N-methylbenzamide

(E)-methyl 3-(N-methylbenzamido)acrylate

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

N-Formyl-N-methylbenzamide