FIELD: chemistry.
SUBSTANCE: invention relates to a process for the preparation of triiodophenol compounds of formula 2, comprising the iodination of a 3,5-disubstituted phenol of formula 1 or a salt thereof, in an aqueous medium, with molecular iodine in the presence of iodic acid, wherein R and R', represent, independently, a group of formula -NHR1 or -NR2R3, wherein each R1, R2 and R3, is, independently, a straight or branched C1-C6 alkyl group which is optionally substituted by one or more groups selected from hydroxyl (-OH), C1-C5 alkoxy and hydroxyalkoxy groups. Also a process for the preparation of a compounds of formula 5, wherein: R and R' represent, independently, a group of formula 2, and R4 and R5, are, independently, hydrogen or a straight or branched C1-C6 alkyl group, optionally substituted by one or more hydroxyl or C1-C6 alkoxy groups, comprising: (a) preparing a triiodophenol compound of formula 2, said process further comprising: (b) reacting said compound of formula 2, either as such or comprising the phenolic OH-group in the form of a salt with an alkali metal, with a compound of formula R4HN(C=O)CH(R5)Z (formula 3), wherein R4 and R5 are, independently, as defined above, and Z is a halogen atom selected from chlorine or bromine, or a leaving group selected from methanesulfonyloxy, benzenesulfonyloxy, nitrobenzenesulfonyloxy, and toluensulfonyloxy, to obtain a compound of formula 4; and (c) subjecting said compound of formula 4 to Smiles' rearrangement in the presence of a base to obtain the compound of formula 5.
EFFECT: preparation of triiodinated aromatic compounds of adequate purity for the synthesis of desired iodinated compound (x-ray contrast media).
15 cl, 5 dwg, 8 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD OF IODISING AROMATIC COMPOUNDS | 2009 |
|
RU2469997C2 |
METHOD OF IODINATION OF AROMATIC COMPOUNDS | 2010 |
|
RU2506254C2 |
METHOD OF PRODUCING IODISING AGENT | 2010 |
|
RU2528402C2 |
PROCESS FOR PREPARATION OF LEVOTHYROXINE AND SALTS THEREOF | 2015 |
|
RU2673540C2 |
1-PHENYL-2,3-DIMETHYL-4-IODOPYRALOZONE-5 (IODOANTIPYRINE) SYNTHESIS METHOD | 2009 |
|
RU2401830C1 |
METHOD OF SYNTHESIS OF N,N-DISUBSTITUTED AMINOMETHYLSTYRENES OR ALPHA-AMINOMETHYLSTYRENES | 2014 |
|
RU2673231C1 |
METHOD OF DETERMINING METHYLPHENOLS IN AQUEOUS MEDIA | 2011 |
|
RU2459203C1 |
METHOD OF PRODUCING SULPHATED DERIVATIVE OF 3,5-DIIODO-O-[3-IODOPHENYL]-L-TYROSINE | 2012 |
|
RU2610093C2 |
METHOD OF PRODUCING SULPHATED DERIVATIVE OF 3,5-DIIODO-O-[3-IODOPHENYL]-L-TYROSINE | 2018 |
|
RU2708244C1 |
METHOD OF PRODUCING SULPHATED DERIVATIVE OF 3,5-DIIODO-O-[3-IODOPHENYL]-L-TYROSINE | 2012 |
|
RU2662826C1 |
Authors
Dates
2015-09-20—Published
2011-06-09—Filed