N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide

Base Information

• Chemical Name: N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide
• CAS No.: 737824-52-1
• Molecular Formula: C₂₁H₁₉N₃O₃S₂
• Molecular Weight: 425.532
• Mol file: 737824-52-1.mol

Synonyms:N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide

Chemical Property of N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide

There total 9 articles about N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide 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%

N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamide (737824-51-0) + (p-nitrobenzyl)triphenylphosphonium bromide (2767-70-6) → N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide (737824-52-1)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

ethyl 2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazole-4-carboxylate (737824-50-9) → N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide (737824-52-1)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2: manganese(IV) oxide / methanol; chloroform / 13 h / 20 °C / Inert atmosphere

3: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With manganese(IV) oxide; lithium aluminium tetrahydride; potassium tert-butylate; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; 3: |Wittig Olefination;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

C14H16N2O2S2 (874900-00-2) → N-{5-[4-(methylthio)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide (737824-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: manganese(IV) oxide / methanol; chloroform / 13 h / 20 °C / Inert atmosphere

2: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With manganese(IV) oxide; potassium tert-butylate; In methanol; chloroform; N,N-dimethyl-formamide; 2: |Wittig Olefination;

DOI:10.1016/j.bmc.2013.02.048

upstream raw materials:

ethyl 2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazole-4-carboxylate

N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamide

(p-nitrobenzyl)triphenylphosphonium bromide

C₁₄H₁₆N₂O₂S₂

Downstream raw materials:

N-{5-[4-(methylsulfonyl)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide

N-{4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide

tert-butyl {(Z)-{[4-(2-{2-acetamido-5-[4-(methylsulfanyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-[(tert-butoxycarbonyl)amino]methylene}carbamate

di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate