5-{4-[2-(Methylpyridin-2-ylamino)ethoxy]benzylidene}-thiazolidine-2,4-dione

Base Information

• Chemical Name: 5-{4-[2-(Methylpyridin-2-ylamino)ethoxy]benzylidene}-thiazolidine-2,4-dione
• CAS No.: 122320-74-5
• Molecular Formula: C18H17N3O3S
• Molecular Weight: 355.417
• Hs Code.: 2934999090
• European Community (EC) Number: 602-492-8
• DSSTox Substance ID: DTXSID701134964
• Mol file: 122320-74-5.mol

Synonyms:122320-74-5;5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]benzylidene]-2,4-thiazolidinedione;C18 H17 N3 O3 S;5-[4-[2-[N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene]thiazolidine-2,4-dione;5-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione;ROSIGLITAZONE TARTRATE IMPURITY I;SCHEMBL1847035;2,4-tiazolidinadiona, 5-[[4-[2-(metil-2-piridinilamino)etoxi]fenil]metileno]-;HCDYSWMAMRPMST-UHFFFAOYSA-N;DTXSID701134964;BCP05335;PD055749;FT-0672124;5-[4-[2-[N-(Methyl)-N-(2-pyridyl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione;5-{4-[2-(methylpyridin-2-ylamino)ethoxy]benzylidene}-thiazolidine-2,4-dione

Chemical Property of 5-{4-[2-(Methylpyridin-2-ylamino)ethoxy]benzylidene}-thiazolidine-2,4-dione

Chemical Property:

• Appearance/Colour: Yellow crystalline powder
• Refractive Index: 1.688
• PKA: 7.26±0.20(Predicted)
• PSA: 96.83000
• Density: 1.361 g/cm³
• LogP: 3.24950
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 355.09906259
• Heavy Atom Count: 25
• Complexity: 518

Purity/Quality:

99% ^*data from raw suppliers

5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]-benzylidene]-2,4-thiazolidinedione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CCOC1=CC=C(C=C1)C=C2C(=O)NC(=O)S2)C3=CC=CC=N3
• Uses: (5E)-Rosiglitazone is the E-isomer of Rosiglitazone (R693505). Rosiglitazone is an insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).

Technology Process of 5-{4-[2-(Methylpyridin-2-ylamino)ethoxy]benzylidene}-thiazolidine-2,4-dione

There total 6 articles about 5-{4-[2-(Methylpyridin-2-ylamino)ethoxy]benzylidene}-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: 95.3%

thiazoline-2,4-dione (2295-31-0) + 4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde (122321-03-3) → 5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione (122320-74-5)

Guidance literature:

With pyrrolidine; acetic acid; In toluene; for 3h; Heating; Reflux;

Reference yield: 80.0%

2-(N-methyl-N-(pyridin-2-yl)amino)ethanol (122321-04-4) + 5-(4-fluorobenzylidene)-1,3-thiazolidine-2,4-dione → 5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione (122320-74-5)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 100 ℃; for 4h;

DOI:10.1002/cctc.201900490

Reference yield:

C9H6FNO → 5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione (122320-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: C₉H₁₄N₂OS / dimethyl sulfoxide / 48 h / 600 °C / 7500.75 Torr

2: potassium hydroxide / dimethyl sulfoxide / 4 h / 100 °C

With C₉H₁₄N₂OS; potassium hydroxide; In dimethyl sulfoxide;

DOI:10.1002/cctc.201900490

upstream raw materials:

thiazoline-2,4-dione

4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

2-chloropyridine

Downstream raw materials:

rosiglitazone

Refernces

• 1、 Zhou, Hui,Zhang, Rui,Mu, Sen,Zhang, Hui,Lu, Xiao-Bing. "Organocatalytic Cyclization of COS and Propargylic Derivatives to Value-Added Heterocyclic Compounds". . p. 5728 - 5732. Retrieved 2019/06/04.
• 2、 -. "PROCESS FOR PREPARING THIAZOLIDINEDIONES". Page/Page column 13-14. . Retrieved 2008/06/13.