ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate

Base Information

• Chemical Name: ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• CAS No.: 161798-01-2
• Molecular Formula: C14H13NO4S
• Molecular Weight: 291.328
• Hs Code.: 2934100090
• Mol file: 161798-01-2.mol

Synonyms:Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate;

Chemical Property of ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate

Chemical Property:

• Melting Point: 116 °C
• Refractive Index: 1.625
• Boiling Point: 446.7 °C at 760 mmHg
• PKA: 6.81±0.20(Predicted)
• Flash Point: 223.9 °C
• PSA: 104.73000
• Density: 1.335 g/cm³
• LogP: 2.81330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

≥98.0% ^*data from raw suppliers

Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate is a product prepared via reaction 4-Hydroxybenzene-1-benzothiomide with ethyl-2-chloro acetoacetate. An antibacterial agent and antifungal activity against C.albicans.

Technology Process of ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate

There total 11 articles about ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-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: 96.6%

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester) (161797-99-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2)

Guidance literature:

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester); With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃; for 0.2h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -10 ℃; for 0.5h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; hexane; at 10 ℃; for 0.166667h; Time; Inert atmosphere;

Reference yield: 91.2%

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester) (161797-99-5) + hexamethylenetetramine (100-97-0) → ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2)

Guidance literature:

With methanesulfonic acid; boric acid; In cyclohexane; at 75 - 100 ℃; for 7h; Temperature; Reagent/catalyst; Solvent;

Reference yield: 80.0%

ethyl 2-bromoacetoacetate (84911-18-2,609-13-2) + hexamethylenetetramine (100-97-0) → ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2)

Guidance literature:

With trifluoroacetic acid; for 20h; Reflux;

DOI:10.3390/molecules21081023

upstream raw materials:

ethyl 2-chloro-3-oxo-butyrate

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

hexamethylenetetramine

4-hydroxythiobenzamide

Downstream raw materials:

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

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

Refernces

• 1、 -. "Method for synthesizing febuxostat and intermediate thereof". Paragraph 0109-0184. . Retrieved 2020/05/02.
• 2、 Sam Daniel Prabu,Lakshmanan, Sivalingam,Thirumurugan,Ramalakshmi,Arul Antony. "Synthesis, molecular docking, DFT study of novel N-benzyl-2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxamide derivatives and their antibacterial activity". . p. 619 - 626. Retrieved 2020/02/06.