Disalicylimide

Base Information

• Chemical Name: Disalicylimide
• CAS No.: 1972-71-0
• Molecular Formula: C14H11NO4
• Molecular Weight: 257.246
• UNII: QN42R68E24
• DSSTox Substance ID: DTXSID30877409
• Nikkaji Number: J1.605.605G
• Wikidata: Q82859201
• ChEMBL ID: CHEMBL580072
• Mol file: 1972-71-0.mol

Synonyms:disalicyloyl-amine;N-Salicyloylsalicylamid;JS-2-90;Disalicylamide;2-hydroxy-N-(2-hydroxybenzoyl)benzamide;

Chemical Property of Disalicylimide

Chemical Property:

• Melting Point: 203-204 °C
• Boiling Point: 503.8±50.0 °C(Predicted)
• PKA: 7.48±0.30(Predicted)
• PSA: 86.63000
• Density: 1.382±0.06 g/cm3(Predicted)
• LogP: 2.05890
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Sonicated), Pyridine (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 257.06880783
• Heavy Atom Count: 19
• Complexity: 312

Purity/Quality:

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

Disalicylimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)NC(=O)C2=CC=CC=C2O)O
• Uses: Disalicylimide is an impurity of Deferasirox (D228650), an orally active tridentate iron chelator.

Technology Process of Disalicylimide

There total 21 articles about Disalicylimide 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: 90.0%

salicylamide (65-45-2) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 2-hydroxy-N-(2-hydroxybenzoyl)benzamide (1972-71-0)

Guidance literature:

salicylic acid; With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 50 ℃; for 2h;

salicylamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene; acetonitrile; at 5 ℃; for 24h;

With hydrogenchloride; In water; N,N-dimethyl-formamide; toluene; acetonitrile; at 20 ℃; for 2h;

Reference yield: 76.0%

2-(benzyloxy)-N-[(2-hydroxyphenyl)carbonyl]benzamide (1369525-64-3) → 2-hydroxy-N-(2-hydroxybenzoyl)benzamide (1972-71-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 18h;

DOI:10.1021/jm2015183

Reference yield: 75.0%

salicyloyl chloride (1441-87-8) → 2-hydroxy-N-(2-hydroxybenzoyl)benzamide (1972-71-0)

Guidance literature:

salicyloyl chloride; With 1,1,1,3,3,3-hexamethyl-disilazane; In toluene; at 0 - 10 ℃; for 1h; Inert atmosphere;

With ethanol; Reflux;

upstream raw materials:

phenyl Salicylate

salicylamide

phosgene

hydrogenchloride

Downstream raw materials:

2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one

C₂₂H₁₄N₄O₂

C₂₃H₁₇N₃O₄

C₂₂H₁₅N₃O₄

Refernces

• 1、 Amanlou, Massoud,Azizian, Homa,Balalaie, Saeed,Biglar, Mahmood,Fathi Vavsari, Vaezeh,Mahernia, Shabnam,Sadeghi Alavijeh, Nahid,Salehi Ashani, Razieh,Sheysi, Niloofar. "Synthesis, Biological Evaluation and Molecular Docking of Deferasirox and Substituted 1,2,4-Triazole Derivatives as Novel Potent Urease Inhibitors: Proposing Repositioning Candidate". . . Retrieved 2020/05/05.
• 2、 Rao, Vascuri Janardhana,Mukkanti, Kagga,Vekariya,Gupta, P. Badrinadh,Islam, Aminul. "Synthesis and characterization of related substances of deferasirox, an iron (Fe3+) chelating agent". . p. 3200 - 3210. Retrieved 2012/11/13.