3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone

Base Information

• Chemical Name: 3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone
• CAS No.: 191166-45-7
• Molecular Formula: C₁₉H₁₉N₃O₆S₂
• Molecular Weight: 449.508
• Mol file: 191166-45-7.mol

Synonyms:3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone

Chemical Property of 3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone

There total 1 articles about 3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone 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:

5-bromopyridine-3-ol (74115-13-2) → 3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone (191166-45-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 86 percent / dimethylformamide / 4 h / Heating

2.1: 80 percent / K₂CO₃ / dimethylformamide / 5 h / Heating

3.1: 1.80 g / Et₃N; H₂S / pyridine / 1 h

4.1: 81 percent / ethanol / 7.25 h / ice-cooling -> reflux

5.1: 1.06 g / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 20 °C

6.1: 83 percent / Et₃N / acetonitrile / 8 h / Heating

7.1: 408 mg / Et₃N; H₂S / pyridine / 4 h

8.1: KHCO₃ / tetrahydrofuran / 2.1 h / ice-cooling -> room temperature

8.2: 95 percent / TFAA; pyridine / tetrahydrofuran / 1 h / ice-cooling

9.1: 547 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 20 °C

10.1: 97 percent / acetic anhydride / 2 h / 100 °C

With hydrogen sulfide; acetic anhydride; potassium carbonate; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Alkylation / 3.1: Addition / 4.1: Cyclization / 5.1: Oxidation / 6.1: Substitution / 7.1: Addition / 8.1: Alkylation / 8.2: Cyclization / 9.1: Oxidation / 10.1: Rearrangement;

DOI:10.1246/bcsj.71.1391

Reference yield:

3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)-6(1H)-pyridone (191166-45-7) → 6-{2-[1-(t-butoxycarbonylamino)-2-(p-methoxybenzylthio)ethyl]-4-thiazolyl}-3-ethoxy-2,5-bis(4-ethoxycarbonyl-2-thiazolyl)pyridine

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / 4-dimethylaminopyridine; N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

2: 93 percent / LiCl / Pd(PPh₃)4 / tetrahydrofuran / 22 h / Heating

3: 25 percent / H₂O; N-bromosuccinimide / dimethylsulfoxide / 0.17 h

4: 1.9 mg / MnO₂ / CH₂Cl₂ / 20 °C

5: 48.2 mg / ethanol / 1.5 h / 0 °C / Heating

With dmap; manganese(IV) oxide; N-Bromosuccinimide; water; N-ethyl-N,N-diisopropylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; 1: Esterification / 2: Condensation / 3: Addition / 4: Oxidation / 5: Cyclization;

DOI:10.1246/bcsj.71.1391

upstream raw materials:

5-bromopyridine-3-ol