Process for the preparation of a dicarboxylic acid di-chloride
AssigneeFructamine S.p.A.
InventorsMarina Mauro, Carlo Felice Viscardi, Massimo Gatti, Nicola Desantis
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Abstract
The present invention refers to a Process for the preparation of S-(-)-5-2-(acetyloxy)-1-oxopropyl!amino!-2,4,6-triiodo-1,3-benzenedicarb oxylic acid dichloride of formula (I) comprising the reaction between S-(-)-2-(acetyloxy)!propionic acid chloride and 5-amino-2,4,6-triiodo-, 1,3-benzenedicarboxylic acid dichloride, in an aprotic dipolar solvent and in presence of a halogenhydric acid.
Claims17
Process for the preparation of S-(-)-5-2-(acetyloxy)-1-oxopropyl!amino!-2,4,6-triiodo-1,3-benzenedicarb oxylic acid dichloride of formula (I) ##STR4## comprising the reaction between S-(-)-2-(acetyloxy)!propionic acid chloride and 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride, in an aprotic dipolar solvent and in presence of a halogenhydric acid.
Process for the preparation of S-(-)-5-2-(acetyloxy)-1-oxopropyl!amino!-2,4,6-triiodo-1,3-benzenedicarb oxylic acid dichloride comprising the following steps:
- a) catalytic hydrogenation of 5-nitro-1,3-benzenedicarboxylic acid in neutral or basic environment, which gives an aqueous solution of 5-amino-1,3-benzenedicarboxylic acid sodium salt;
- b) direct iodination of the 5-amino-1,3-benzenedicarboxylic acid sodium salt solution deriving from step a), without further purification, with a solution of ICl in HCl, being the 5-amino-1,3-benzenedicarboxylic acid sodium salt solution previously added with HCl and H.sub.2 SO.sub.4 to give 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid;
- c) chlorination of the 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride, in heterogeneous phase between 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid and thionyl chloride, in a solvent selected from:
- (C.sub.7 -C.sub.16) linear or branched hydrocarbons, (C.sub.7 -C.sub.8) aromatic hydrocarbons, 1,1,1-trichloroethane, n-butylacetate, diglyme (diethylenglycoledimethylether), and in the presence of a catalytic amount of a tertiary amine, to give 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride;
- d) reaction between S-(-)-2-(acetyloxy)!propionic acid chloride and 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride, in an aprotic dipolar solvent and in presence of a halogenhydric acid.
Dependencies are inferred from the claim text.