5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N₁-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine

Base Information

• Chemical Name: 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N₁-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine
• CAS No.: 1393736-21-4
• Molecular Formula: C₂₆H₂₅N₅O₂
• Molecular Weight: 439.517

Synonyms:5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N₁-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine

Chemical Property of 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N₁-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine

Chemical Property:

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Technology Process of 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N₁-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine

There total 8 articles about 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N₁-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine 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: 66.0%

→ 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N1-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine (1393736-21-4)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; for 2h; under 1551.49 - 2068.65 Torr;

Reference yield: 65.9%

N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methylcarbamoyl-2-nitroaniline (1372407-00-5) → 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N1-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine (1393736-21-4)

Guidance literature:

With 5% Pd/C; hydrogen; In ethanol; under 1551.49 - 2068.65 Torr;

DOI:10.1021/jm3007678

Reference yield:

5-chloro-N1-(4-cyanophenyl)-4-methoxycarbonyl-2-nitroaniline (1372129-84-4) → 5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N1-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine (1393736-21-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 190 °C / Microwave irradiation

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

2.2: 3 h / 20 °C

3.1: sodium hydroxide / tetrahydrofuran; water; methanol / 4 h / 20 °C

3.2: pH 2 - 3

4.1: thionyl chloride / dichloromethane / 3 h / 20 °C / Reflux

5.1: tetrahydrofuran; water / 0.5 h / 0 °C

6.1: hydrogen; 5% Pd/C / ethanol / 1551.49 - 2068.65 Torr

With thionyl chloride; 5% Pd/C; potassium tert-butylate; hydrogen; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm3007678

upstream raw materials:

5-chloro-N¹-(4-cyanophenyl)-4-methoxycarbonyl-2-nitroaniline

N₁-(4'-cyanophenyl)-5-(2'',6''-dimethyl-4''-formylphenoxy)-4-methoxycarbonyl-2-nitroaniline

N₁-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methoxycarbonyl-2-nitroaniline

N₁-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-carboxy-2-nitroaniline

Downstream raw materials:

C₂₇H₂₃N₅O₂

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