Ethyl 2-(4-chlorophenylamino)-4-thiazolecarboxylate

Base Information

• Chemical Name: Ethyl 2-(4-chlorophenylamino)-4-thiazolecarboxylate
• CAS No.: 165682-93-9
• Molecular Formula: C12H11ClN2O2S
• Molecular Weight: 282.751
• Hs Code.: 2934100090
• European Community (EC) Number: 870-593-6
• DSSTox Substance ID: DTXSID30699845
• Nikkaji Number: J3.448.079F
• Wikidata: Q82630906
• ChEMBL ID: CHEMBL3593861
• Mol file: 165682-93-9.mol

Synonyms:ethyl 2-((4-chlorophenyl)amino)thiazole-4-carboxylate;O4I2 compound

Chemical Property of Ethyl 2-(4-chlorophenylamino)-4-thiazolecarboxylate

Chemical Property:

• Boiling Point: 408.1±51.0 °C(Predicted)
• PKA: 1.48±0.10(Predicted)
• PSA: 79.46000
• Density: 1.382±0.06 g/cm3(Predicted)
• LogP: 3.78980
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 282.0229765
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

99%+, ^*data from raw suppliers

O4I2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CSC(=N1)NC2=CC=C(C=C2)Cl
• Uses: O4I2 is a potent inducer of Oct3/4 expression.

Technology Process of Ethyl 2-(4-chlorophenylamino)-4-thiazolecarboxylate

There total 3 articles about Ethyl 2-(4-chlorophenylamino)-4-thiazolecarboxylate 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: 89.0%

ethyl Bromopyruvate (70-23-5) + N-(4-chlorophenyl)thiourea (3696-23-9) → ethyl 2-((4-chlorophenyl)amino)thiazole-4-carboxylate (165682-93-9)

Guidance literature:

In ethanol; Reflux;

DOI:10.1021/acs.jmedchem.5b00226

Reference yield:

2-oxo-propionic acid ethyl ester (617-35-6) → ethyl 2-((4-chlorophenyl)amino)thiazole-4-carboxylate (165682-93-9)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / Cooling

2: sodium carbonate / neat (no solvent) / Milling

With bromine; sodium carbonate; In neat (no solvent);

DOI:10.1016/j.ejmech.2016.07.033

Reference yield:

4-chloro-aniline (106-47-8) → ethyl 2-((4-chlorophenyl)amino)thiazole-4-carboxylate (165682-93-9)

Guidance literature:

Multi-step reaction with 3 steps

1: acetone / 12.33 h / 20 - 40 °C

2: ethylamine / water / 12 h / 20 °C

3: ethanol / 150 °C / Microwave irradiation

With ethylamine; In ethanol; water; acetone;

DOI:10.1021/acs.jmedchem.9b01244

upstream raw materials:

ethyl Bromopyruvate

N-(4-chlorophenyl)thiourea

2-oxo-propionic acid ethyl ester

4-chloro-aniline

Downstream raw materials:

N-(4-chlorophenyl)-4-[(4-methyl-1-piperidinyl)carbonyl]-1,3-thiazol-2-amine

2-[(4-chlorophenyl)amino]-1,3-thiazole-4-carboxylic acid

Refernces

• 1、 Kumar, Sunil,Aggarwal, Ranjana,Kumar, Virender,Sadana, Rachna,Patel, Bhumi,Kaushik, Pawan,Kaushik, Dhirender. "Solvent-free synthesis of bacillamide analogues as novel cytotoxic and anti-inflammatory agents". . p. 718 - 726. Retrieved 2016/08/15.
• 2、 Washburn, David G.,Holt, Dennis A.,Dodson, Jason,McAtee, Jeff J.,Terrell, Lamont R.,Barton, Linda,Manns, Sharada,Waszkiewicz, Anna,Pritchard, Christina,Gillie, Dan J.,Morrow, Dwight M.,Davenport, Elizabeth A.,Lozinskaya, Irina M.,Guss, Jeffrey,Basilla, Jonathan B.,Negron, Lorena Kallal,Klein, Michael,Willette, Robert N.,Fries, Rusty E.,Jensen, Timothy C.,Xu, Xiaoping,Schnackenberg, Christine G.,Marino Jr., Joseph P.. "The discovery of potent blockers of the canonical transient receptor channels, TRPC3 and TRPC6, based on an anilino-thiazole pharmacophore". supporting information. p. 4979 - 4984. Retrieved 2013/09/02.