(S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide

Base Information

• Chemical Name: (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide
• CAS No.: 1309831-74-0
• Molecular Formula: C₁₈H₂₀ClNO₃S
• Molecular Weight: 365.881
• Mol file: 1309831-74-0.mol

Synonyms:(S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide

Chemical Property of (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide

There total 1 articles about (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide 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: 83.0%

2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde (132283-68-2) + (S)-p-toluenesulfinimide (188447-91-8) → (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide (1309831-74-0)

Guidance literature:

With titanium(IV) tetraethanolate; In dichloromethane; for 3h; Reflux;

DOI:10.1021/jo2007237

Reference yield: 58.0%

(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene (1309831-72-8) + (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide (1309831-74-0) → (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline (1309831-80-8) + (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline (1309831-76-2)

Guidance literature:

(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/jo2007237

Reference yield:

(S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide (1309831-74-0) → S-(-)-Norlaudanosine (4747-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 12 h / -78 - 20 °C

2.1: trifluoroacetic acid / methanol / 3 h / 0 °C

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

With tert.-butyl lithium; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; pentane;

DOI:10.1021/jo2007237

upstream raw materials:

2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde

(S)-p-toluenesulfinimide

Downstream raw materials:

(1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline

(1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline

(1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

(1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline