5-(2,4,5-Trimethoxybenzyl)-2,4-thiazolidinedione

Base Information

• Chemical Name: 5-(2,4,5-Trimethoxybenzyl)-2,4-thiazolidinedione
• CAS No.: 79525-00-1
• Molecular Formula: C₁₃H₁₅NO₅S
• Molecular Weight: 297.332
• DSSTox Substance ID: DTXSID701000565
• Nikkaji Number: J59.621C
• Mol file: 79525-00-1.mol

Synonyms:BRN 5600016;5-(2,4,5-Trimethoxybenzyl)-2,4-thiazolidinedione;2,4-Thiazolidinedione, 5-(2,4,5-trimethoxybenzyl)-;2,4-Thiazolidinedione, 5-((2,4,5-trimethoxyphenyl)methyl)-;79525-00-1;SCHEMBL11156581;DTXSID701000565;LS-151349;4-Hydroxy-5-[(2,4,5-trimethoxyphenyl)methyl]-1,3-thiazol-2(5H)-one

Chemical Property of 5-(2,4,5-Trimethoxybenzyl)-2,4-thiazolidinedione

Chemical Property:

• Vapor Pressure: 2.11E-09mmHg at 25°C
• Boiling Point: 480.8°Cat760mmHg
• Flash Point: 244.6°C
• Density: 1.306g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 297.06709375
• Heavy Atom Count: 20
• Complexity: 378

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1CC2C(=O)NC(=O)S2)OC)OC

Technology Process of 5-(2,4,5-Trimethoxybenzyl)-2,4-thiazolidinedione

There total 5 articles about 5-(2,4,5-Trimethoxybenzyl)-2,4-thiazolidinedione 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:

asaraldehyde (4460-86-0,14374-62-0) → 5-(2,4,5-trimethoxybenzyl)thiazolidine-2,4-dione (79525-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87.3 percent / piperidine, benzoic acid / toluene / 4 h / Heating

2: 82.4 percent / H₂ / 10percent Pd-C / methanol / 760 Torr / Ambient temperature

3: 91.5 percent / 60percent NaH, NCS / tetrahydrofuran / 0.5 h / Ambient temperature

4: 1.) 2N KOH / 1.) MeOH, r.t., 1 h, 2.) AcOH, reflux, 3 h

5: 1N HCl / ethanol / 10 h / Heating

With piperidine; hydrogenchloride; potassium hydroxide; N-chloro-succinimide; hydrogen; sodium hydride; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1248/cpb.31.560

Reference yield:

diethyl 2-(2,4,5-trimethoxybenzylidene)malonate (14374-64-2,57724-31-9) → 5-(2,4,5-trimethoxybenzyl)thiazolidine-2,4-dione (79525-00-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 82.4 percent / H₂ / 10percent Pd-C / methanol / 760 Torr / Ambient temperature

2: 91.5 percent / 60percent NaH, NCS / tetrahydrofuran / 0.5 h / Ambient temperature

3: 1.) 2N KOH / 1.) MeOH, r.t., 1 h, 2.) AcOH, reflux, 3 h

4: 1N HCl / ethanol / 10 h / Heating

With hydrogenchloride; potassium hydroxide; N-chloro-succinimide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol;

DOI:10.1248/cpb.31.560

Reference yield:

2-imino-5-(2,4,5-trimethoxybenzyl)thiazolidin-4-one (79525-12-5) → 5-(2,4,5-trimethoxybenzyl)thiazolidine-2,4-dione (79525-00-1)

Guidance literature:

With hydrogenchloride; In ethanol; for 10h; Yield given; Heating;

DOI:10.1248/cpb.31.560

upstream raw materials:

2-imino-5-(2,4,5-trimethoxybenzyl)thiazolidin-4-one

asaraldehyde

diethyl 2-(2,4,5-trimethoxybenzylidene)malonate

diethyl 2-(2,4,5-trimethoxybenzyl)malonate

Refernces