N₂-(2-chlorophenyl)-N₂,N₈-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

Base Information

• Chemical Name: N₂-(2-chlorophenyl)-N₂,N₈-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide
• CAS No.: 1189810-72-7
• Molecular Formula: C₂₂H₁₉ClN₂O₃S
• Molecular Weight: 426.923

Synonyms:N₂-(2-chlorophenyl)-N₂,N₈-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

Chemical Property of N₂-(2-chlorophenyl)-N₂,N₈-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

Chemical Property:

Purity/Quality:

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Technology Process of N₂-(2-chlorophenyl)-N₂,N₈-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

There total 9 articles about N₂-(2-chlorophenyl)-N₂,N₈-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide 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: 26.0%

8-bromo-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (1189810-76-1) + methylamine (74-89-5) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → N2-(2-chlorophenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide (1189810-72-7)

Guidance literature:

With trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]-dipalladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 150 ℃; for 0.333333h; under 760.051 Torr; Sealed vial; Microwave irradiation;

DOI:10.1021/jm2007084

Reference yield:

ethyl 4-(3-bromophenoxy)butanoate (157245-84-6) → N2-(2-chlorophenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide (1189810-72-7)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 48 h / 50 °C

2: polyphosphoric acid; celite / toluene / 5 h / 110 °C

3: N,N-dimethyl-formamide / 20 °C

4: potassium carbonate / N,N-dimethyl-formamide / 50 °C

5: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 50 °C

6: thionyl chloride / 2 h / 80 °C

7: triethylamine / dichloromethane / 0 - 20 °C

8: trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]-dipalladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.33 h / 150 °C / 760.05 Torr / Sealed vial; Microwave irradiation

With thionyl chloride; trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]-dipalladium(II); lithium hydroxide monohydrate; water; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm2007084

Reference yield:

methyl 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylate (1189815-76-6) → N2-(2-chlorophenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide (1189810-72-7)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 50 °C

2: thionyl chloride / 2 h / 80 °C

3: triethylamine / dichloromethane / 0 - 20 °C

4: trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]-dipalladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.33 h / 150 °C / 760.05 Torr / Sealed vial; Microwave irradiation

With thionyl chloride; trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]-dipalladium(II); lithium hydroxide monohydrate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm2007084

upstream raw materials:

ethyl 4-(3-bromophenoxy)butanoate

methyl 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylate

8-bromo-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

methylamine

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