3-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]-2-oxo-4H-imidazol-5-olate

Base Information

• Chemical Name: 3-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]-2-oxo-4H-imidazol-5-olate
• CAS No.: 7261-97-4
• Molecular Formula: C14H10 N4 O5
• Molecular Weight: 314.257
• Hs Code.: 2934990002
• European Community (EC) Number: 230-684-8
• Wikipedia: Dantrolene
• NCI Thesaurus Code: C61697,C61698
• RXCUI: 3105,3106
• Mol file: 7261-97-4.mol

Synonyms:Dantrium;Dantrolene;Dantrolene Sodium;Sodium, Dantrolene

Chemical Property of 3-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]-2-oxo-4H-imidazol-5-olate

Chemical Property:

• Melting Point: 279-280°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 453.94°C (rough estimate)
• PKA: 7.68±0.10(Predicted)
• PSA: 120.73000
• Density: 1.57 g/cm³
• LogP: 2.53040
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 313.05729440
• Heavy Atom Count: 23
• Complexity: 536

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dantrolene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Autonomic Agents: Muscle Relaxants, Central
• Canonical SMILES: C1C(=NC(=O)N1N=CC2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-])[O-]
• Isomeric SMILES: C1C(=NC(=O)N1/N=C/C2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-])[O-]
• Recent ClinicalTrials: A Clinical Trial of Dantrolene Sodium in Pediatric and Adult Patients With Wolfram Syndrome
• Uses: Dantrolene acts as a skeletal muscle relaxant through inhibition of Ca2+ release through ryanodine receptor channels.
• Therapeutic Function: Muscle relaxant

Technology Process of 3-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]-2-oxo-4H-imidazol-5-olate

There total 9 articles about 3-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]-2-oxo-4H-imidazol-5-olate 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: 98.0%

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt (14663-23-1) → dantrolene (7261-97-4)

Guidance literature:

With acetic acid; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 96.0%

1-aminohydantoin (6301-02-6) + 5-(4-nitrophenyl)-2-furaldehyde (7147-77-5) → dantrolene (7261-97-4)

Guidance literature:

With hydrogenchloride; In water; N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1039/c7gc00497d

Reference yield: 94.0%

5-(4-nitrophenyl)-2-furaldehyde (7147-77-5) + 1-aminohydantoin hydrochloride (2827-56-7) → 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]imino]-2,4-imidazolidinedione (7261-97-4)

Guidance literature:

In acetonitrile; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201805644

upstream raw materials:

1-aminohydantoin

5-(4-nitrophenyl)-2-furaldehyde

1-aminohydantoin hydrochloride

furfural

Downstream raw materials:

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

3-<3-(N-tert-butoxycarbonylamino)-1-oxopropyl-1-<<5-(4-nitrophenyl)-2-furanyl>methylene>amino>-2,4-imidazolidinedione

Refernces

• 1、 Colacino, Evelina,Porcheddu, Andrea,Solin, Niclas,Wang, Lei,Yuan, Yusheng. "Mechanochemical Preparation of Protein : hydantoin Hybrids and Their Release Properties". . . Retrieved 2021/12/14.
• 2、 -. "Dantrolene prodrug and method for using same". Paragraph 0308-0310; 0313-0315. . Retrieved 2020/07/15.