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US 5,177,261 AGranted
Synthesis of ioversol using chloroacetyl chloride
AssigneeMallinckrodt Medical, Inc.
InventorsWilliam Z. McCarthy, Mills T. Kneller, Youlin Lin, David H. White
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Abstract
The use of chloroacetylchloride as an alternative or substitute reagent for acetoxychloride in the synthesis of N,N'- bis (2,3-dihydroxypropyl)-5-N-(2-hydroxyethyl)glycolamido-2,4,6-triiodoisophth alamide.
Claims13
A process for the production of ioversol [5chloroacetamido-N,N'-bis(2,3-diacetoxypropyl)-2,4,6triiodoisophthalamide ] from 5-amino-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalmaide, comprising the steps of:
- a. reacting N,N-dimethylacetamide, chloroacetylchloride and 5-amino-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide to undergo a N-alkylation reaction to form an amide reaction mixture;
- b. diluting said amide reaction mixture with an organic solvent;
- c. extracting said amide reaction mixture with an aqueous solution to undergo a N-acylation reaction to recover 5-chloroacetamido-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamid e, a N-alkyl, and
- d. hydrolyzing said N-alkyl to produce ioversol.
1 more element
A process for the production of ioversol comprising the steps of:
- a. reacting N,N-dimethylacetamide, chloroacetylchloride and 5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide to undergo a N-acylation reaction to form a secondary amide reaction mixture;
- b. diluting said secondary amide reaction mixture with an organic solvent;
- c. extracting said secondary amide reaction mixture with an aqueous solution to recover 5-chloroacetamido-N,N'-bis[2,3-di(chloroacetoxypropyl)]-2,4,6-triiodoisoph thalamide,
- d. N-alkalizing 5-chloracetamide -N,N'-bis[2,3-di(chloro-acetoxypropyl)] -2,4,6-triiodoisopthalamide to produce a N-alkyl mixture, and
- e. hydrolyzing said N-alkyl mixture to produce ioversol.
2 more elements
Dependencies are inferred from the claim text.