5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide

Base Information

• Chemical Name: 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide
• CAS No.: 671207-79-7
• Molecular Formula: C₃₃H₂₈ClIN₂O₄
• Molecular Weight: 678.954

Synonyms:5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide

Chemical Property of 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide

Chemical Property:

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Technology Process of 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide

There total 7 articles about 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide 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: 98.0%

(E)-4-bromo-N-phenylbut-2-enamide + N-(5-chloro-2-iodo-phenyl)-N-(4-methoxy-benzyl)-3-oxo-3-phenyl-propionamide (671207-78-6) → 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide (671207-79-7)

Guidance literature:

N-(5-chloro-2-iodo-phenyl)-N-(4-methoxy-benzyl)-3-oxo-3-phenyl-propionamide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 0 ℃; for 1h;

(E)-4-bromo-N-phenylbut-2-enamide; In tetrahydrofuran; toluene; at 0 ℃; for 2h;

DOI:10.1016/S0014-827X(03)00166-6

Reference yield:

5-chloro-2-iodoaniline (6828-35-9) → 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide (671207-79-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 66 percent / NaI / dimethylformamide / 2 h / 80 °C

2.1: 97 percent / pyridine / toluene / 0.75 h / 0 °C

3.1: 92 percent / aq. LiOH / tetrahydrofuran / 18 h / 20 °C

4.1: 65 percent / 4-(dimethylamino)pyridine; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / CH₂Cl₂ / 1.25 h / 0 - 20 °C

5.1: [(CH₃)3Si]2NNa / tetrahydrofuran / -78 - 0 °C

5.2: 52 percent / tetrahydrofuran / 0.25 h / 20 °C

6.1: 95 percent / CF₃COOH / 0.5 h

7.1: [(CH₃)3Si]2NK / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

7.2: 98 percent / tetrahydrofuran; toluene / 2 h / 0 °C

With pyridine; dmap; lithium hydroxide; sodium hexamethyldisilazane; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0014-827X(03)00166-6

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 5-benzoyl-hex-2-enedioic acid 6-[(5-chloro-2-iodo-phenyl)-(4-methoxy-benzyl)-amide] 1-phenylamide (671207-79-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 66 percent / NaI / dimethylformamide / 2 h / 80 °C

2.1: 97 percent / pyridine / toluene / 0.75 h / 0 °C

3.1: 92 percent / aq. LiOH / tetrahydrofuran / 18 h / 20 °C

4.1: 65 percent / 4-(dimethylamino)pyridine; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / CH₂Cl₂ / 1.25 h / 0 - 20 °C

5.1: [(CH₃)3Si]2NNa / tetrahydrofuran / -78 - 0 °C

5.2: 52 percent / tetrahydrofuran / 0.25 h / 20 °C

6.1: 95 percent / CF₃COOH / 0.5 h

7.1: [(CH₃)3Si]2NK / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

7.2: 98 percent / tetrahydrofuran; toluene / 2 h / 0 °C

With pyridine; dmap; lithium hydroxide; sodium hexamethyldisilazane; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0014-827X(03)00166-6

upstream raw materials:

N-(5-chloro-2-iodo-phenyl)-N-(4-methoxy-benzyl)-3-oxo-3-phenyl-propionamide

5-chloro-2-iodoaniline

p-methoxybenzyl chloride

N-(5-chloro-2-iodo-phenyl)-N-(4-methoxybenzyl)-malonamic acid methyl ester

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