N-((3-Ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenylacetamide

Base Information

• Chemical Name: N-((3-Ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenylacetamide
• CAS No.: 3747-06-6
• Deprecated CAS: 171812-78-5
• Molecular Formula: C14H14 N2 O2 S2
• Molecular Weight: 306.409
• European Community (EC) Number: 223-143-2
• DSSTox Substance ID: DTXSID9063164
• Nikkaji Number: J217.643B
• Wikidata: Q76144236
• Mol file: 3747-06-6.mol

Synonyms:3747-06-6;N-[(Z)-(3-ethyl-4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]-N-phenylacetamide;DTXSID9063164;HMS1414D21;EINECS 223-143-2;STK396451;AKOS000520168;Z56788827;N-((3-Ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenylacetamide;N-[(3-Ethyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl]-N-phenylacetamide

Chemical Property of N-((3-Ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenylacetamide

Chemical Property:

• Vapor Pressure: 2.89E-07mmHg at 25°C
• Melting Point: 123-125 °C (polymorph)(Solv: methanol (67-56-1))
• Boiling Point: 420.1°Cat760mmHg
• PKA: -0.56±0.20(Predicted)
• Flash Point: 207.9°C
• PSA: 98.01000
• Density: 1.38g/cm³
• LogP: 2.69900
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 306.04967004
• Heavy Atom Count: 20
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

N-(3-ETHYL-4-OXO-2-THIOXO-THIAZOLIDIN-5-YLIDENEMETHYL)-N-PHENYL-ACETAMIDE AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C(=O)C(=CN(C2=CC=CC=C2)C(=O)C)SC1=S
• Isomeric SMILES: CCN1C(=O)/C(=C/N(C2=CC=CC=C2)C(=O)C)/SC1=S

Technology Process of N-((3-Ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenylacetamide

There total 11 articles about N-((3-Ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenylacetamide 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: 77.9%

5-anilinomethylidene-3-etylrhodanine (118050-10-5) + acetic anhydride (108-24-7) → 5-acetanilidomethylidene-3-ethylrhodanine (3747-06-6)

Guidance literature:

With triethylamine; at 110 ℃; for 0.5h;

DOI:10.1021/jm970590k

Reference yield: 70.0%

3-ethyl-5-((phenylamino)methylene)-2-thioxothiazolidin-4-one (39542-83-1) + acetic anhydride (108-24-7) → N-(3-ethyl-4-oxo-2-thioxothiazolidin-5-ylidenemethyl)-N-phenylacetamide (3747-06-6)

Guidance literature:

With triethylamine; for 10h; Heating;

Reference yield:

3-ethylrhodanin (7648-01-3) → N-(3-ethyl-4-oxo-2-thioxothiazolidin-5-ylidenemethyl)-N-phenylacetamide (3747-06-6)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 1 h / 70 °C

2: 9.46 g / triethylamine / 0.5 h / 100 °C

With triethylamine; In acetonitrile;

DOI:10.1016/j.bmc.2006.08.035

upstream raw materials:

3-ethylrhodanin

N,N'-diphenylformamidine

3-ethyl-5-((phenylamino)methylene)-2-thioxothiazolidin-4-one

acetic anhydride

Downstream raw materials:

3-ethyl-5-[2-(4-phenyl-4H-benzo[f]quinolin-3-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one

3-ethyl-2-thioxo-5-[2-(4-p-tolyl-4H-benzo[f]quinolin-3-ylidene)-ethylidene]-thiazolidin-4-one

3-ethyl-5-{2-[4-(4-methoxy-phenyl)-4H-benzo[f]quinolin-3-ylidene]-ethylidene}-2-thioxo-thiazolidin-4-one

3-ethyl-5-[2-(1-phenyl-1H-quinolin-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one