5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione

Base Information

• Chemical Name: 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione
• CAS No.: 141200-53-5
• Molecular Formula: C₂₃H₂₀N₂O₃S
• Molecular Weight: 404.489
• Mol file: 141200-53-5.mol

Synonyms:5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione

Chemical Property of 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione

There total 10 articles about 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione 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: 50.0%

5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-hydroxypropyl>benzyl>thiazolidine-2,4-dione (125531-74-0) → 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione (141200-53-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1021/jm00088a022

Reference yield:

terephthalaldehyde mono(diethylacetal) (81172-89-6) → 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione (141200-53-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / diethyl ether / -75 °C

2: 60 percent / manganese dioxide / toluene / 18 h / Heating

3: 1.) sodium hydride / 1.) ether, RT, 25 min, 2.) ether, ethanol, reflux, 6 h

4: 1.) sodium hydride / 1.) THF, RT, 0.5 h, 2.) THF, reflux, 48 h

5: conc. HCl / acetic acid / 5 h / Heating

6: 71 percent / piperidine / ethanol / 24 h / Heating

7: 81 percent / H₂ / Pd/C / tetrahydrofuran / 24 h / 2585.7 Torr / Ambient temperature

8: 46 percent / sodium borohydride / propan-2-ol / 2 h

9: 50 percent / p-toluenesulfonic acid hydride / toluene / Heating

With piperidine; hydrogenchloride; manganese(IV) oxide; sodium tetrahydroborate; hydrogen; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; acetic acid; isopropyl alcohol; toluene;

DOI:10.1021/jm00088a022

Reference yield:

4-(diethoxymethyl)acetophenone (125532-06-1) → 5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione (141200-53-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) sodium hydride / 1.) ether, RT, 25 min, 2.) ether, ethanol, reflux, 6 h

2: 1.) sodium hydride / 1.) THF, RT, 0.5 h, 2.) THF, reflux, 48 h

3: conc. HCl / acetic acid / 5 h / Heating

4: 71 percent / piperidine / ethanol / 24 h / Heating

5: 81 percent / H₂ / Pd/C / tetrahydrofuran / 24 h / 2585.7 Torr / Ambient temperature

6: 46 percent / sodium borohydride / propan-2-ol / 2 h

7: 50 percent / p-toluenesulfonic acid hydride / toluene / Heating

With piperidine; hydrogenchloride; sodium tetrahydroborate; hydrogen; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; acetic acid; isopropyl alcohol; toluene;

DOI:10.1021/jm00088a022

upstream raw materials:

5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-hydroxypropyl>benzyl>thiazolidine-2,4-dione

terephthalaldehyde mono(diethylacetal)

4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]benzaldehyde

1-<4-(diethoxymethyl)phenyl>ethanol