1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

Base Information

• Chemical Name: 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile
• CAS No.: 1001085-39-7
• Molecular Formula: C₁₇H₁₅ClN₂OS
• Molecular Weight: 330.838

Synonyms:1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

Chemical Property of 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

Chemical Property:

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Technology Process of 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

There total 4 articles about 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile 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: 80.0%

1-mercapto-5,6,7,8-tetrahydroisoquinolin-3-ol (1001088-34-1) + 3-hydroxy-1-mercapto-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (126799-70-0) + 1-bromomethyl-2-chlorobenzene (611-17-6) → 1-(2-chlorobenzylsulfanyl)-5,6,7,8-tetrahydroisoquinolin-3-ol (1001085-40-0) + 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (1001085-39-7)

Guidance literature:

With potassium carbonate; In ethanol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2011.09.058

Reference yield: 15.0%

carbon disulfide (75-15-0,12122-00-8) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 1-bromomethyl-2-chlorobenzene (611-17-6) + malononitrile (109-77-3) → 1-(2-chlorobenzylsulfanyl)-5,6,7,8-tetrahydroisoquinolin-3-ol (1001085-40-0) + 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (1001085-39-7)

Guidance literature:

carbon disulfide; cyclohexanone; malononitrile; With triethylamine; N,N-dimethyl-formamide; In methanol; at 20 ℃; for 36h;

With sodium hydroxide; at 20 - 150 ℃; for 7h;

1-bromomethyl-2-chlorobenzene; With potassium carbonate; In methanol; at 20 ℃; for 1h;

Reference yield:

3-amino-1-thioxo-2(1H)-5,6,7,8-tetrahydro-benzothiopyran-4-carbonitrile (5275-11-6) → 1-(2-chlorobenzylsulfanyl)-3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (1001085-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 7 h / 150 °C

2: potassium carbonate / ethanol / 1 h / 20 °C

With potassium carbonate; sodium hydroxide; In ethanol;

DOI:10.1016/j.bmcl.2011.09.058

upstream raw materials:

1-mercapto-5,6,7,8-tetrahydroisoquinolin-3-ol

3-hydroxy-1-mercapto-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

1-bromomethyl-2-chlorobenzene

3-amino-1-thioxo-2(1H)-5,6,7,8-tetrahydro-benzothiopyran-4-carbonitrile

Downstream raw materials:

1-(2-chlorobenzylthio)-2-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

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