1-(((5-(4-Chlorophenyl)-2-furanyl)methylene)amino)-2,4-imidazolidinedione

Base Information

• Chemical Name: 1-(((5-(4-Chlorophenyl)-2-furanyl)methylene)amino)-2,4-imidazolidinedione
• CAS No.: 14663-26-4
• Molecular Formula: C14H10 Cl N3 O3
• Molecular Weight: 303.705
• ChEMBL ID: CHEMBL3276938
• Mol file: 14663-26-4.mol

Synonyms:14663-26-4;BRN 0686024;1-(((5-(4-Chlorophenyl)-2-furanyl)methylene)amino)-2,4-imidazolidinedione;1-[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione;1-[(E)-[5-(4-chlorophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione;2,4-Imidazolidinedione, 1-(((5-(4-chlorophenyl)-2-furanyl)methylene)amino)-;C14H10ClN3O3;SCHEMBL978316;CHEMBL3276938;LS-79111;Z91274053

Chemical Property of 1-(((5-(4-Chlorophenyl)-2-furanyl)methylene)amino)-2,4-imidazolidinedione

Chemical Property:

• Melting Point: 275-277 °C
• PKA: 7.70±0.10(Predicted)
• PSA: 78.40000
• Density: 1.496g/cm³
• LogP: 2.69950
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 303.0410689
• Heavy Atom Count: 21
• Complexity: 449

Purity/Quality:

1-[[5-(4-Chlorophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC(=O)N1N=CC2=CC=C(O2)C3=CC=C(C=C3)Cl
• Isomeric SMILES: C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)C3=CC=C(C=C3)Cl
• Uses: 1-[[5-(4-Chlorophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione is an intermediate of Azimilide Dihydrochloride(A926950), which is an oral type III potassium channel blocker agent that blocks both the rapid activating component and the slow activating component of the delayed rectifier potassium current. Both preclinical and clinical studies have demonstrated the efficacy of azimilide and its safety in the treatment of supraventricular and ventricular tachyarrhythmia. Azimilide also is being studied in a worldwide multicenter trial for prevention of sudden cardiac death in patients after myocardial infarction.

Technology Process of 1-(((5-(4-Chlorophenyl)-2-furanyl)methylene)amino)-2,4-imidazolidinedione

There total 4 articles about 1-(((5-(4-Chlorophenyl)-2-furanyl)methylene)amino)-2,4-imidazolidinedione 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: 89.1%

5-(4-chlorophenyl)-2-furaldehyde (34035-03-5) + 1-aminohydantoin hydrochloride (2827-56-7) → 1-[5-(4-chloro-phenyl)-furan-2-ylmethyleneamino]-imidazolidine-2,4-dione (14663-26-4)

Guidance literature:

In water; at 80 ℃; for 4h;

Reference yield: 83.0%

1-aminohydantoin (6301-02-6) + 5-(4-chlorophenyl)-2-furaldehyde (34035-03-5) → 1-[5-(4-chloro-phenyl)-furan-2-ylmethyleneamino]-imidazolidine-2,4-dione (14663-26-4)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1007/s00044-021-02711-y

Reference yield:

4-chloro-aniline (106-47-8) → 1-[5-(4-chloro-phenyl)-furan-2-ylmethyleneamino]-imidazolidine-2,4-dione (14663-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; sodium nitrite / water / 0.33 h / 70 °C

2: water / 4 h / 80 °C

With hydrogenchloride; sodium nitrite; In water;

upstream raw materials:

5-(4-chlorophenyl)-2-furaldehyde

1-aminohydantoin hydrochloride

4-chloro-aniline

furfural

Downstream raw materials:

N-methyl-acetamide

Refernces

• 1、 -. "A phenyl [...] hERG potassium ion channel of small molecule fluorescent probe and its application (by machine translation)". Paragraph 0040; 0057. . Retrieved 2016/11/24.