267881-76-5

Basic information

• Product Name: 1,3-Benzenedicarboxamide, 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-
• CAS NO: 267881-76-5
• Molecular Formula: C14H21N3O6
• Molecular Weight: 327.337
• Mol File: 267881-76-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3-Benzenedicarboxamide, 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenedicarboxamide, 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-(267881-76-5)
• EPA Substance Registry System: 1,3-Benzenedicarboxamide, 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-(267881-76-5)

Safety Data

• Hazardous Substances Data: 267881-76-5(Hazardous Substances Data)

Upstream product

• 10552-75-7 dibutyl 5-nitroisophthalate 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 
• 13290-96-5 dimethyl 5-nitroisophthalate 
• 60166-97-4 N,N'-bis-(2-hydroxy-1-hydroxymethylethyl)-5-nitroisophthalamide 
• 25351-79-5 5-amino-isophthalic acid dibutyl ester 
• 534-03-2 serinol 
• 99-27-4 dimethyl 5-aminoisophthalate 

Downstream Products

• 60166-98-5 S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide 
• 60166-93-0 Iopamidol 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF IOPAMIDOL

The present invention discloses a process for the preparation of Iopamidol of formula (II) and comprising the following steps: a) reacting the Compound (I) wherein X is OR2 or R3, and wherein R2 and R3 are a Ci-C6 linear or branched alkyl, C3-C6 cycloalkyl, C6 aryl, optionally substituted with a group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl and phenyl, with the acylating agent (S)-2-(acetyloxy)propanoyl chloride in a reaction medium to provide the acetyloxy derivative of Compound (I); b) hydrolyzing the intermediate from step a) with an aqueous solution at a pH comprised from 0 to 7, by adding water or a diluted alkaline solution such as sodium hydroxide or potassium hydroxide, freeing the hydroxyls from the boron-containing protective groups, obtaining the N-(S)-2-(acetyloxy)propanoyl derivative of Compound (II); c) alkaline hydrolysis to restore the (S)-2-(hydroxy)propanoyl group and to obtain lopamidol (II) and optional recovery of the boron derivative from the solution obtained in step b). The boron-containing protective group is versatile, efficient and recyclable. A one-pot synthesis, without intermediate isolation is provided, leading to a decreasing of recovered and recycled solvents and a significant increasing in the yield, representing a significant advantage in terms of cost-effectiveness of the entire process and environmental awareness.

Process for the preparation of n,n-substituted 5-amino-1,3-benzenedicarboxamides

The invention relates to a process for the preparation of a compound of formula (I), wherein R represents a 2,3-dihydroxy-1-propyl or a 1,3-dihydroxy-2-propyl radical, via direct amidation of a dialkyl ester of 5-amino-1,3-benzenedicarboxylic acid of formula (V), wherein R1 represents a straight or branched (C1-C4)-alkyl group, with at least the stoichiometric amount of an amine of formula H2NR.