Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

Base Information

• Chemical Name: Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• CAS No.: 161798-03-4
• Molecular Formula: C18H21NO4S
• Molecular Weight: 347.435
• Hs Code.: 2934100090
• European Community (EC) Number: 700-743-7
• DSSTox Substance ID: DTXSID90447849
• Nikkaji Number: J2.383.422G
• Wikidata: Q72474996
• Mol file: 161798-03-4.mol

Synonyms:161798-03-4;Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate;5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester;Ethyl 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate;Ethyl2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate;EC 700-743-7;2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester;5-Thiazolecarboxylic acid, 2-(3-formyl-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester;5-Thiazolecarboxylicacid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester;SCHEMBL457516;DTXSID90447849;BCP23185;MFCD13194811;AKOS005145710;AC-5910;2-(3-formyl-4-isobutoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester;AS-19561;A3589;AM20090756;FT-0659111;C73087;Q-103513;5-Thiazolecarboxylicacid,2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-,ethyl ester;ethyl 2-[3-formyl-4-(2-methyl propoxy)phenyl]-4-methyl-5-thiazolcarboxylate

Chemical Property of Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

Chemical Property:

• Vapor Pressure: 5.68E-10mmHg at 25°C
• Refractive Index: 1.566
• Boiling Point: 495.9 °C at 760 mmHg
• PKA: 1.39±0.10(Predicted)
• Flash Point: 253.7 °C
• PSA: 93.73000
• Density: 1.183
• LogP: 4.14250
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 347.11912932
• Heavy Atom Count: 24
• Complexity: 431

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=C(S1)C2=CC(=C(C=C2)OCC(C)C)C=O)C
• Uses: Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate is an impurity of Febuxostat (F229000), which is a xanthine oxidase/xanthine dehydrogenase inhibitor, used for treatment of hyperuricemia and chronic gout.

Technology Process of Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

There total 16 articles about Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate 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: 97.0%

3-formyl-4-isobutoxythiobenzamide + ethyl 2-chloro-3-oxo-butyrate (609-15-4) → 2-(3-formyl-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (161798-03-4)

Guidance literature:

In N,N-dimethyl-formamide; at 60 ℃; for 4h;

Reference yield: 96.0%

Isobutyl bromide (78-77-3) + ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2) → 2-(3-formyl-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (161798-03-4)

Guidance literature:

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate; With potassium carbonate; In N,N-dimethyl-formamide; for 0.166667h; Inert atmosphere;

Isobutyl bromide; In N,N-dimethyl-formamide; at 100 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.chempr.2020.12.004

Reference yield: 92.7%

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2) + isobutyl p-toluenesulfonate (4873-56-7) → 2-(3-formyl-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (161798-03-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 - 110 ℃; Temperature;

upstream raw materials:

Isobutyl bromide

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester)

ethyl 2-chloro-3-oxo-butyrate

Downstream raw materials:

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Refernces

• 1、 Gundluru, Mohan,Badavath, Vishnu Nayak,Shaik, Haroon Yasmin,Sudileti, Murali,Nemallapudi, Bakthavatchala Reddy,Gundala, Sravya,Zyryanov, Grigory V.,Cirandur, Suresh Reddy. "Design, synthesis, cytotoxic evaluation and molecular docking studies of novel thiazolyl α-aminophosphonates". . p. 1139 - 1160. Retrieved 2020/11/16.
• 2、 -. "Method for synthesizing febuxostat and intermediate thereof". Paragraph 0187-0190; 0197-0204. . Retrieved 2020/05/02.