Phenylimidazolidine preparation process

Details Phenylimidazolidine preparation process Phenylimidazolidine preparation process

1998-06-10

2000-08-22

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5483205, 5483211, 5483201, C07D23372, C07D49110

Patent

active

061074888

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a new preparation process for phenyl imidazolidine derivatives.
Therefore a subject of the present invention is a new preparation process for the products of formula (I): ##STR3## in which: R.sub.1 and R.sub.2, identical or different, are chosen from the hydrogen atom, halogen atoms and the following radicals: alkyl, alkenyl, alkynyl, alkyloxy, alkenyloxy, alkynyloxy, phenyl, phenoxy, nitro, crifluoro-methyl, acyl, cyano, amino, monoalkylamino, dialkylamino, free, esterified, amidified or salified carboxy, and arylalkyl radicals, all these radicals being optionally substituted by one or more substituents chosen from halogen atoms, the following radicals: optionally esterified, etherified or protected hydroxyl, alkoxy, alkenyloxy, alkynyloxy, trifluoromethyl, mercapto, cyano, acyl, acyloxy, free, esterified, amidified or salified carboxy, amino, mono- and dialkylamino, arylthio and cyclic radicals containing 3 to 6 members, the alkyl, alkenyl or alkynyl radicals being more optionally interrupted by one or more oxygen, nitrogen or sulphur atoms, sulphoxide or sulphone, alkyl, alkenyl or alkynyl radical, R.sub.4 and R.sub.5 : radical, optionally substituted by one or more substituents chosen from halogen atoms, the optionally esterified, etherified or protected hydroxyl radical and phenylthio and alkylthio radicals, in which the sulphur atom can be oxidized into the sulphoxide or sulphone and being optionally substituted by one or more radicals chosen from halogen atoms and optionally esterified, etherified or protected hydroxyl radicals, free, esterified, amidified or salified carboxy radicals, amino, mono- and dialkylamino radicals, oxygen or sulphur atom, diastereoisomeric isomer forms, as well as the addition salts with mineral and organic acids or mineral and organic bases of said products of formula (I), ##STR4## is prepared, in which w represents a halogen atom or a hydantoin derivative of formula: ##STR5## in which R'.sub.4 and R'.sub.5 have the meanings indicated above for R.sub.4 and R.sub.5 in which the optional reactive functions are optionally protected, ##STR6## either first of all, a compound of formula (III): ##STR7## in which Hal represents a halogen atom and V represents a hydrogen atom or a halogen atom, then the compound of formula (B): ##STR8## in order to obtain the product of formula (A.sub.1): ##STR9## corresponding to the product of formula (A) in which W represents the dimethylhydantoin radical: ##STR10## or N-bromosuccinimide in dimethylformamide, or the compound of formula (III) as defined above, in order to obtain the product of formula (A.sub.2): ##STR11## in which Hal represents a bromine atom or another halogen tom, which can be reacted with a compound of formula (IV): ##STR12## in which R'.sub.4 and R'.sub.5 have the meanings indicated above, in order to obtain the product of formula (A.sub.3): ##STR13## corresponding to the product of formula (A) in which W represents the radical: ##STR14## in which R'.sub.4 and R'.sub.5 have the meanings indicated above, b) if necessary and if desired, the product of formula (A) thus obtained is subjected to one or more of the following reactions, in any order: ##STR15## in which A.sup..crclbar. represent an anion of a halogen atom or of a halogenated derivative and W has the meaning indicated above, which can be subjected to a halogenation reaction in order to obtain the product of formula (F.sub.1): ##STR16## in which Hal and W have the meanings indicated above, which can be subjected to a substitution reaction on the halogen atom by a metallic derivative of formula (VI): for R.sub.1, in which the optional reactive functions are optionally protected, in order to obtain the product of formula (F.sub.2): ##STR17## in which R'.sub.1 and W have the meanings indicated above, ii) a halogenation reaction in order to obtain the product of formula (F.sub.3): ##STR18## in which Hal represents a halogen atom and W has the meaning indicated above, which can: metallic derivative of formula (VII): for R.sub.2 in which th

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