196309-04-3

Basic information

• Product Name: N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2,2-dimethyl-1,3-dioxan-5-yl)(hydroxyacetyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide
• CAS NO: 196309-04-3
• Molecular Weight: 877.208
• Mol File: 196309-04-3.mol

Chemical Properties

• CAS DataBase Reference: N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2,2-dimethyl-1,3-dioxan-5-yl)(hydroxyacetyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2,2-dimethyl-1,3-dioxan-5-yl)(hydroxyacetyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide(196309-04-3)
• EPA Substance Registry System: N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2,2-dimethyl-1,3-dioxan-5-yl)(hydroxyacetyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide(196309-04-3)

Safety Data

• Hazardous Substances Data: 196309-04-3(Hazardous Substances Data)

Relevant articles and documents

Smiles rearrangement as a tool for the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamides: Main pathway and side reactions

In the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamides 1a-h from 2a-h two conditions using stoichiometric amounts of base (method A - aq NaOH at 50°C; method B - MeONa in DMF at r, t.) were used. Yields are good to excellent provided that the right conditions are chosen. Primary amides 2a,b give 1a,b with method B only, whereas with method A extensive hydrolysis of the CONH2 moiety is observed. N-Methyl derivatives 2c,d afford 1c,d with either method. However, with method B long reaction times lead to the formation of large amounts of benzoxazinones, 4c,d. Under the same conditions, the pattern of side products which are formed from N-(hydroxyalkyl)phenoxyacetamides 2e-g is further complicated by: i) intramolecular cyclizations leading to bicyclic (7f,g) and tricyclic structures (5) ii) N-deacylation; iii) double Smiles rearrangement reactions.