N₁-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide

Base Information

• Chemical Name: N₁-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide
• CAS No.: 1392442-09-9
• Molecular Formula: C₂₇H₂₅N₃O₈S
• Molecular Weight: 551.577

Synonyms:N₁-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide

Chemical Property of N₁-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide

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Technology Process of N₁-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide

There total 6 articles about N₁-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide 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: 90.0%

2-amino-6-nitrobenzothiazole (6285-57-0) + 2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid (763903-09-9) → N1-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide (1392442-09-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2012.08.021

Reference yield:

(Z)-5-(3-tert-butyldimethylsilyloxy-4-methoxystyryl)-1,2,3-trimethoxybenzene (121042-95-3) → N1-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide (1392442-09-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 5 - 10 °C

2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C

3: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 20 °C

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 24 h / 20 °C

With lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2012.08.021

Reference yield:

(E)-1-(3',4',5'-Trimethoxyphenyl)-2-(4''-methoxy-3''-tert-butyldimethylsiloxyphenyl)ethene (121042-96-4) → N1-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide (1392442-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1: ethanol / UV-irradiation

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 5 - 10 °C

3: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C

4: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 20 °C

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 24 h / 20 °C

With lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2012.08.021

upstream raw materials:

(Z)-5-(3-tert-butyldimethylsilyloxy-4-methoxystyryl)-1,2,3-trimethoxybenzene

(E)-1-(3',4',5'-Trimethoxyphenyl)-2-(4''-methoxy-3''-tert-butyldimethylsiloxyphenyl)ethene

2-amino-6-nitrobenzothiazole

2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid

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