phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone

Base Information

• Chemical Name: phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone
• CAS No.: 402717-64-0
• Molecular Formula: C₂₄H₂₁NO₅S
• Molecular Weight: 435.5

Synonyms:phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone

Chemical Property of phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone

Chemical Property:

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Technology Process of phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone

There total 2 articles about phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone 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: 57.0%

4′′-methyl-N-[(3,4-methylenedioxyphenyl)ethyl]benzenesulfonamide (64880-90-6) + α-chloro-α-(phenylthio)acetophenone (67655-17-8) → phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone (402717-64-0)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 - 20 ℃; for 5h;

DOI:10.1016/S0040-4039(01)01998-0

Reference yield:

1-phenyl-2-(phenylthio)ethanone (16222-10-9) → phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone (402717-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / N-chlorosuccinimide; benzoyl peroxide / CCl₄

2: 57 percent / SnCl₄ / CH₂Cl₂ / 5 h / -78 - 20 °C

With N-chloro-succinimide; tin(IV) chloride; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; 2: Pictet-Spengler condensation;

DOI:10.1016/S0040-4039(01)01998-0

Reference yield: 87.0%

phenyl-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone (402717-64-0) → (7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-methanone (471908-63-1)

Guidance literature:

With aluminum oxide; potassium fluoride; for 0.00277778h; microwave irradiation;

DOI:10.1055/s-2002-31923

upstream raw materials:

4′′-methyl-N-[(3,4-methylenedioxyphenyl)ethyl]benzenesulfonamide

α-chloro-α-(phenylthio)acetophenone

1-phenyl-2-(phenylthio)ethanone

Downstream raw materials:

1-benzoyl-6,7-methylenedioxyisoquinoline

(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-methanone

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