N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide

Base Information

• Chemical Name: N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide
• CAS No.: 60166-98-5
• Molecular Formula: C14H18I3N3O6
• Molecular Weight: 705.027
• Hs Code.: 2924296000
• UNII: JK9TZ8JY3W
• Mol file: 60166-98-5.mol

Synonyms:60166-98-5;N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide;JK9TZ8JY3W;5-Amino-N1,N3-bis(1,3-dihydroxypropan-2-yl)-2,4,6-triiodoisophthalamide;5-amino-1-N,3-N-bis(1,3-dihydroxypropan-2-yl)-2,4,6-triiodobenzene-1,3-dicarboxamide;(N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoiso-phthalamide;5-Amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodobenzene-1,3-dicarboxamide;1,3-Benzenedicarboxamide, 5-amino-N1,N3-bis(2-hydroxy-1-(hydroxymethyl)ethyl)-2,4,6-triiodo-;6-Hydroxy-3,4-dihydro-1H-quinolin-2-one N,N'-bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide);Iopamidol impurity A;UNII-JK9TZ8JY3W;SCHEMBL2763618;BCP34387;5-amino-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide;F81345;5-Amino-N,N'-bis(1,3-dihydroxy-2-propyl)-2,4,6-triiodoisophthalamide;5-Amino-N1,N3-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide;N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethy]-5-amino-2,4,6-tri-iodoisophthalamide;Iopamidol Related Compound A;Iopamidol Impurity A

Chemical Property of N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide

Chemical Property:

• Boiling Point: 688.7±55.0 °C(Predicted)
• PKA: 10.98±0.46(Predicted)
• PSA: 165.14000
• Density: 2.386±0.06 g/cm3(Predicted)
• LogP: 0.61160
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 704.8330
• Heavy Atom Count: 26
• Complexity: 441

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-N,N''-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(CO)NC(=O)C1=C(C(=C(C(=C1I)N)I)C(=O)NC(CO)CO)I)O
• Uses: 5-Amino-N,N''-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (Iopamidol EP Impurity A) is an impurity in the synthesis of Iopamidol (I735600), a nonionic radiocontrast medium. Diagnostic aid (radiopaque medium).

Technology Process of N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide

There total 10 articles about N,N'-Bis-(1,3-dihydroxy-2-propyl)-5-amino-2,4,6-triiodoisophthalamide 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: 89.9%

5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide (267881-76-5) → S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (60166-98-5)

Guidance literature:

With potassium iodate; sulfuric acid; iodine; sodium sulfate; In water; at 65 - 80 ℃; for 47h; Concentration; Time;

Reference yield: 47.0%

serinol (534-03-2) + 5-amino-2,4,6-triiodoisophthalic acid dichloride (37441-29-5) → S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (60166-98-5)

Guidance literature:

for 0.5h; Milling;

Reference yield:

5-aminoisophthalic acid (99-31-0) → S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (60166-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / aq. potassium iododichloride / H₂O / 18 h / 55 - 60 °C

2: 92 percent / thionyl chloride

3: N,N-dimethyl-acetamide / 16 h / Ambient temperature

With thionyl chloride; potassium dichloroiodate; In N,N-dimethyl acetamide; water;

DOI:10.1021/jo00085a023

upstream raw materials:

serinol

5-amino-2,4,6-triiodoisophthalic acid dichloride

5-aminoisophthalic acid

2,4,6-triiodo-5-aminoisophthalic acid

Downstream raw materials:

Iopamidol

5-acetylamino-N,N'-bis(1,3-dihydroxy-2-propyl)-2,4,6-triiodoisophthalamide

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF IOPAMIDOL". Page/Page column 25-26. . Retrieved 2015/05/26.
• 2、 -. "Process for the preparation of n,n-substituted 5-amino-1,3-benzenedicarboxamides". . . Retrieved 2008/06/13.