Optimisation of the preparation and isolation of 5-amino-2,4,6-triiodoisophthalic acid dichloride

H.J.M. Gijsen; H.C.C.K. Bakel, van; W. Zwaan; L.A. Hulshof

doi:10.1021/op980055+

Optimisation of the preparation and isolation of 5-amino-2,4,6-triiodoisophthalic acid dichloride

H.J.M. Gijsen, H.C.C.K. Bakel, van, W. Zwaan, L.A. Hulshof

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Abstract

A scaleable process for the chlorination of 5-amino-2,4,6-triiodoisophthalic acid to the corresponding acid chloride, a building block for the synthesis of iodinated X-ray contrast agents, has been developed. Two dimeric byproducts have been isolated and assigned structures consistent with an amide and an anhydride. Hydrolysis of the N-sulfinyl intermediate and simultaneous crystallisation of the phthalic acid chloride have been optimised by applying fractional factorial design.

Original language	English
Pages (from-to)	38-43
Number of pages	7
Journal	Organic Process Research & Development
Volume	3
Issue number	1
DOIs	https://doi.org/10.1021/op980055+
Publication status	Published - 1999

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abstract = "A scaleable process for the chlorination of 5-amino-2,4,6-triiodoisophthalic acid to the corresponding acid chloride, a building block for the synthesis of iodinated X-ray contrast agents, has been developed. Two dimeric byproducts have been isolated and assigned structures consistent with an amide and an anhydride. Hydrolysis of the N-sulfinyl intermediate and simultaneous crystallisation of the phthalic acid chloride have been optimised by applying fractional factorial design.",

author = "H.J.M. Gijsen and {Bakel, van}, H.C.C.K. and W. Zwaan and L.A. Hulshof",

year = "1999",

doi = "10.1021/op980055+",

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T1 - Optimisation of the preparation and isolation of 5-amino-2,4,6-triiodoisophthalic acid dichloride

AU - Gijsen, H.J.M.

AU - Bakel, van, H.C.C.K.

AU - Zwaan, W.

AU - Hulshof, L.A.

PY - 1999

Y1 - 1999

N2 - A scaleable process for the chlorination of 5-amino-2,4,6-triiodoisophthalic acid to the corresponding acid chloride, a building block for the synthesis of iodinated X-ray contrast agents, has been developed. Two dimeric byproducts have been isolated and assigned structures consistent with an amide and an anhydride. Hydrolysis of the N-sulfinyl intermediate and simultaneous crystallisation of the phthalic acid chloride have been optimised by applying fractional factorial design.

AB - A scaleable process for the chlorination of 5-amino-2,4,6-triiodoisophthalic acid to the corresponding acid chloride, a building block for the synthesis of iodinated X-ray contrast agents, has been developed. Two dimeric byproducts have been isolated and assigned structures consistent with an amide and an anhydride. Hydrolysis of the N-sulfinyl intermediate and simultaneous crystallisation of the phthalic acid chloride have been optimised by applying fractional factorial design.

U2 - 10.1021/op980055+

DO - 10.1021/op980055+

M3 - Article

SN - 1083-6160

VL - 3

SP - 38

EP - 43

JO - Organic Process Research & Development

JF - Organic Process Research & Development

IS - 1

ER -

Optimisation of the preparation and isolation of 5-amino-2,4,6-triiodoisophthalic acid dichloride

Abstract

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