8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Base Information

• Chemical Name: 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• CAS No.: 1428536-63-3
• Molecular Formula: C₂₁H₂₅NO₂S
• Molecular Weight: 355.501

Synonyms:8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Chemical Property of 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Chemical Property:

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Technology Process of 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

There total 4 articles about 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 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:

trans-N-(4-bromobut-2-enyl)-N-(3,4-dimethylphenethyl)-p-toluenesulfonamide → 7,8-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1428536-62-2) + 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1428536-63-3)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 16h; Overall yield = 82 %; regioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.02.012

Reference yield:

3,4-dimethylphenethylamine (17283-14-6) → 7,8-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1428536-62-2) + 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1428536-63-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: bismuth(lll) trifluoromethanesulfonate / dichloromethane / 16 h / 20 °C / Molecular sieve; Inert atmosphere

With bismuth(lll) trifluoromethanesulfonate; potassium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.02.012

Reference yield:

N-(3,4-dimethylphenethyl)toluenesulfonamide (1428536-70-2) → 7,8-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1428536-62-2) + 8,9-dimethyl-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1428536-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: bismuth(lll) trifluoromethanesulfonate / dichloromethane / 16 h / 20 °C / Molecular sieve; Inert atmosphere

With bismuth(lll) trifluoromethanesulfonate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.02.012

upstream raw materials:

N-(3,4-dimethylphenethyl)toluenesulfonamide

p-toluenesulfonyl chloride

3,4-dimethylphenethylamine

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