4-Amino-3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide

Base Information

• Chemical Name: 4-Amino-3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide
• CAS No.: 57037-04-4
• Molecular Formula: C₁₀H₈ClN₃OS₂
• Molecular Weight: 285.778
• DSSTox Substance ID: DTXSID701156643
• Mol file: 57037-04-4.mol

Synonyms:DTXSID701156643;CCG-113647;EU-0047165;SR-01000505523;SR-01000505523-1;4-Amino-3-(4-chlorophenyl)-2,3-dihydro-2-thioxo-5-thiazolecarboxamide;4-amino-3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide;57037-04-4

Chemical Property of 4-Amino-3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 284.9797319
• Heavy Atom Count: 17
• Complexity: 391

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1N2C(=C(SC2=S)C(=O)N)N)Cl

Technology Process of 4-Amino-3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide

There total 1 articles about 4-Amino-3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide 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:

4-Chlorophenyl isothiocyanate (2131-55-7) + cyanoacetic acid amide (107-91-5) → 4-amino-3-(4-chloro-phenyl)-2-thioxo-2,3-dihydro-thiazole-5-carboxylic acid amide (57037-04-4)

Guidance literature:

With sulfur; triethylamine; In N,N-dimethyl-formamide;

Reference yield: 81.0%

4-amino-3-(4-chloro-phenyl)-2-thioxo-2,3-dihydro-thiazole-5-carboxylic acid amide (57037-04-4) + acetic anhydride (108-24-7) → 3-(4-chlorophenyl)-2,3-dihydro-5-methyl-2-thioxothiazolo<4,5-d>pyrimidin-7(6H)-one

Guidance literature:

for 3h; Heating;

DOI:10.1016/0223-5234(93)90002-V

Reference yield:

4-amino-3-(4-chloro-phenyl)-2-thioxo-2,3-dihydro-thiazole-5-carboxylic acid amide (57037-04-4) → 6-[3-[4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl]propyl]-3-(4-chlorophenyl)-2-thioxo-thiazolo[4,5-d]pyrimidin-7-one

Guidance literature:

Multi-step reaction with 4 steps

1: acetic anhydride / 3 h / Reflux

2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 15 h / 100 °C

3: trifluoroacetic acid / dichloromethane / 8 h / 20 °C

4: triethylamine; ammonium chloride / ethanol / Reflux

With acetic anhydride; potassium carbonate; ammonium chloride; triethylamine; trifluoroacetic acid; potassium iodide; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2021.127944

upstream raw materials:

4-Chlorophenyl isothiocyanate

cyanoacetic acid amide

Downstream raw materials:

3-(4-chlorophenyl)-7-oxothiazolo[4,5-d]pyrimidin-2(3H)-thione