2-(O-Tolyl)-thiazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-(O-Tolyl)-thiazole-4-carboxylic acid ethyl ester
• CAS No.: 885278-51-3
• Molecular Formula: C13H13 N O2 S
• Molecular Weight: 247.318
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID60695239
• Wikidata: Q82624360
• Mol file: 885278-51-3.mol

Synonyms:885278-51-3;2-(O-TOLYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;Ethyl 2-(o-tolyl)thiazole-4-carboxylate;Ethyl 2-o-tolylthiazole-4-carboxylate;ethyl 2-(2-methylphenyl)-1,3-thiazole-4-carboxylate;SCHEMBL15754817;DTXSID60695239;FTIWJDSCQBOTIM-UHFFFAOYSA-N;MFCD06738344;AKOS017267536;AB26948;Ethyl2-(o-tolyl)thiazole-4-carboxylate;BS-29642;CS-0208825;FT-0762994;2-o-Tolyl-thiazole-4-carboxylic acid ethyl ester;A861925;2-(O-Tolyl)thiazole-4-carboxylic acid ethyl ester;J-520780

Chemical Property of 2-(O-Tolyl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property:

• Boiling Point: 381.6±44.0 °C(Predicted)
• PKA: 0.11±0.10(Predicted)
• PSA: 67.43000
• Density: 1.188±0.06 g/cm3(Predicted)
• LogP: 3.29520
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 247.06669983
• Heavy Atom Count: 17
• Complexity: 272

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 2-o-tolylthiazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CSC(=N1)C2=CC=CC=C2C

Technology Process of 2-(O-Tolyl)-thiazole-4-carboxylic acid ethyl ester

There total 4 articles about 2-(O-Tolyl)-thiazole-4-carboxylic acid ethyl ester 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: 83.0%

L-cysteine ethyl ester hydrochloride (868-59-7) + 2-methylphenyl aldehyde (529-20-4) → 2-o-tolylthiazole-4-carboxylic acid ethyl ester (885278-51-3)

Guidance literature:

With tert.-butylhydroperoxide; iodine; potassium carbonate; In 1,4-dioxane; at 70 ℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere;

DOI:10.1039/c8ob02826e

Reference yield: 69.0%

2-methylthiobenzamide (53515-19-8) + ethyl Bromopyruvate (70-23-5) → 2-o-tolylthiazole-4-carboxylic acid ethyl ester (885278-51-3) + ethyl 4-(o-tolyl)thiazole-2-carboxylate (1292943-25-9)

Guidance literature:

With pyridine; In ethanol; at 150 ℃; for 1.5h; Microwave irradiation;

DOI:10.1002/jhet.1644

Reference yield: 60.0%

ethyl 2-bromothiazole-4-carboxylate (100367-77-9) + 2-Methylphenylboronic acid (16419-60-6) → 2-o-tolylthiazole-4-carboxylic acid ethyl ester (885278-51-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In water; toluene; at 90 ℃; Inert atmosphere;

upstream raw materials:

ethyl 2-bromothiazole-4-carboxylate

2-Methylphenylboronic acid

2-methylthiobenzamide

ethyl Bromopyruvate

Downstream raw materials:

2-o-tolylthiazole-4-carboxylic acid

2-o-tolylthiazole-4-carboxylic acid (1-pyrrolo[1,2-a]pyrazin-1-yl-pyrrolidin-3-yl)-amide

2-o-tolylthiazole-4-carboxylic acid (1-imidazo[1,2-a]pyrazin-8-yl-pyrrolidin-3-yl)-amide

2-o-tolylthiazole-4-carboxylic acid (1-pyrrolo[1,2-a]pyrazin-1-yl-pyrrolidin-3-yl)-amide

Refernces

• 1、 Khan, Mahmood-ul-Hassan,Hameed, Shahid,Akhtar, Tashfeen,Al-Masoudi, Najim A.,Al-Masoudi, Wasfi A.,Jones, Peter G.,Pannecouque, Christophe. "Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs". . p. 2399 - 2409. Retrieved 2016/10/25.
• 2、 Liang, Jun,Soucy, Valerie Dorman,Tusi, Vickie,Liu, Yanzhou,Zhang, Birong,Lai, Yingjie,Magnuson, Steve,Zhu, Bingyan,Wang, Fangdao,Gu, Jinghao,Zhang, Qingfen,Wu, Yuan,Deng, Wei,Yang, Wenqian. "Steric and electronic factors influence regio-isomeric thiazole formations between substituted benzothioamides and ethyl bromopyruvate". . p. 1137 - 1146. Retrieved 2014/08/05.