3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

Base Information

Chemical Name:3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide
CAS No.:1360060-59-8
Molecular Formula:C₁₉H₂₁ClN₂O₂
Molecular Weight:344.841
Hs Code.:

Synonyms:3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

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Chemical Property of 3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

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Technology Process of 3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

There total 7 articles about 3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)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: 76.0%

: 1360060-74-7
3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzoic acid

: 1360060-59-8
3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

Guidance literature:: With ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 8h;
DOI:10.1016/j.bmc.2011.12.058

Reference yield:

: 39225-17-7
diethyl 4-chlorobenzylphosphonate

: 1360060-59-8
3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium tert-pentoxide / N,N-dimethyl-formamide / 0.33 h / 0 °C

1.2: 2 h / 0 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C

3.1: tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 80 °C

4.1: potassium hydroxide / methanol; water / 1 h / Reflux

5.1: ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 20 °C

With sodium tert-pentoxide; potassium carbonate; ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2011.12.058

Reference yield:

: 120-47-8
Ethyl 4-hydroxybenzoate

: 1360060-59-8
3-[(E)-2-(4-chlorophenyl)vinyl]-4-(2-dimethylaminoethoxy)benzamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine; magnesium chloride / 1,2-dichloro-ethane / 1 h / 40 °C

1.2: 3 h / 70 °C

2.1: sodium tert-pentoxide / N,N-dimethyl-formamide / 0.33 h / 0 °C

2.2: 2 h / 0 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C

4.1: tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 80 °C

5.1: potassium hydroxide / methanol; water / 1 h / Reflux

6.1: ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 20 °C

With sodium tert-pentoxide; potassium carbonate; ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; magnesium chloride; In tetrahydrofuran; methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2011.12.058