(S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione

Base Information

• Chemical Name: (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione
• CAS No.: 750647-37-1
• Molecular Formula: C₁₇H₂₁NO₂S
• Molecular Weight: 303.425
• Mol file: 750647-37-1.mol

Synonyms:(S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione

Chemical Property of (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione

There total 7 articles about (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 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: 81.0%

3-phenyl-pent-2-enoyl chloride (55039-36-6) + (4S)-4-isopropyl-1,3-oxazolidine-2-thione (84272-19-5,104499-08-3) → (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione (750647-37-1)

Guidance literature:

(4S)-4-isopropyl-1,3-oxazolidine-2-thione; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.75h;

3-phenyl-pent-2-enoyl chloride; In tetrahydrofuran; at 0 ℃;

DOI:10.1002/anie.200453889

Reference yield:

(4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0) → (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione (750647-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / Lawesson's reagent / dioxane / 32 h

2.1: NaH / tetrahydrofuran / 0.75 h / 0 °C

2.2: 81 percent / tetrahydrofuran / 0 °C

With Lawessons reagent; sodium hydride; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1002/anie.200453889

Reference yield:

(S)-N-[3-phenyl-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione (750647-29-1) → (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione (750647-37-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 9 h / cooling

2.1: NaBH₄ / tetrahydrofuran / 18 h / 20 °C

3.1: 75 percent / Lawesson's reagent / dioxane / 32 h

4.1: NaH / tetrahydrofuran / 0.75 h / 0 °C

4.2: 81 percent / tetrahydrofuran / 0 °C

With Lawessons reagent; sodium tetrahydroborate; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1002/anie.200453889

upstream raw materials:

3-phenyl-pent-2-enoyl chloride

(4S)-4-isopropyl-1,3-oxazolidine-2-thione

(4S)-4-isopropyl-1,3-oxazolidin-2-one

(S)-N-[3-phenyl-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione