Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1996-01-16
1997-06-10
Barts, Samuel
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 24, 564185, C07C30300
Patent
active
056377533
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR94/00880 filed Jul. 13, 1994.
The present invention relates to a process for the preparation of N-carbonylarylimines of general formula: ##STR3## in which Ar represents an aryl radical and R represents a phenyl or t-butoxy radical.
In the general formula (I), Ar represents an aryl radical and R represents a phenyl or t-butoxy radical.
More particularly, Ar represents a phenyl or .alpha.- or .beta.-naphthyl radical optionally substituted with one or more atoms or radicals chosen from halogen atoms, (fluorine, chlorine, bromine or iodine) and alkyl, alkenyl, alkynyl, aryl, arylalkyl, alkoxy, alkylthio, aryloxy, arylthio, hydroxyl, hydroxyalkyl, mercapto, formyl, acyl, acylamino, aroylamino, alkoxycarbonylamino, amino, alkylamino, dialkylamino, carboxyl, alkoxycarbonyl, carbamoyl, dialkylcarbamoyl, cyano, nitro and trifluoromethyl radicals, it being understood that the alkyl radicals and the alkyl portions of the other radicals contain 1 to 4 carbon atoms, that the alkenyl and alkynyl radicals contain 2 to 8 carbon atoms and that the aryl radicals are phenyl or .alpha.- or .beta.-naphthyl radicals, or alternatively Ar represents a 5-membered aromatic heterocyclic radical containing one or more atoms, which may be identical or different, chosen from nitrogen, oxygen or sulphur atoms, which are optionally substituted with one or more substituents, which may be identical or different, chosen from halogen atoms (fluorine, chlorine, bromine or iodine) and alkyl radicals containing 1 to 4 carbon atoms, aryl radicals containing 6 to 10 carbon atoms, alkoxy radicals containing 1 to 4 carbon atoms, aryloxy radicals containing 6 to 10 carbon atoms, amino radicals, alkylamino radicals containing 1 to 4 carbon atoms, dialkylamino radicals in which each alkyl part contains 1 to 4 carbon atoms, acylamino radicals in which the acyl part contains 1 to 4 carbon atoms, alkoxycarbonylamino radicals containing 1 to 4 carbon atoms, acyl radicals containing 1 to 4 carbon atoms, arylcarbonyl radicals in which the aryl part contains 6 to 10 carbon atoms, cyano, carboxyl and carbamoyl radicals, alkylcarbamoyl radicals in which the alkyl part contains 1 to 4 carbon atoms, dialkylcarbamoyl radicals in which each alkyl part contains 1 to 4 carbon atoms, and alkoxycarbonyl radicals in which the alkoxy part contains 1 to 4 carbon atoms.
More particularly, Ar represents a phenyl, 2- or 3-thienyl or 2- or 3-furyl radical optionally substituted with one or more atoms or radicals, which may be identical or different, chosen from halogen atoms and alkyl, alkoxy, amino, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino and trifluoromethyl radicals.
Even more particularly, Ar represents a phenyl radical optionally substituted with a chlorine or fluorine atom or with an alkyl (methyl), alkoxy (methoxy), dialkylamino (dimethylamino), acylamino (acetylamino) or alkoxycarbonylamino (tert-butoxycarbonylamino) radical or 2- or 3-thienyl or 2- or 3-furyl radical.
According to the invention, the N-carbonylarylimines of general formula (I) may be prepared by the action of a base on a sulphone of general formula: ##STR4## in which Ar and R are defined as above and Ph represents a phenyl radical which is optionally substituted, for example with a methyl radical.
Generally, the process is performed in the presence of an alkali metal carbonate such as sodium carbonate or potassium carbonate, in an organic solvent chosen from ethers (tetrahydrofuran) and aromatic hydrocarbons (benzene or toluene), at a temperature between 50 and 100.degree. C.
The sulphone of general formula (II) may be prepared, optionally in situ, by the action of an alkali metal phenylsulphinate such as sodium phenylsulphinate or potassium phenylsulphinate, on a mixture of an aldehyde of general formula: mixture of water and an aliphatic alcohol containing 1 to 3 carbon atoms (methanol or ethanol), in the presence of an acid such as formic acid.
The N-carbonylarylimines of general formula (I) are particularly useful for stereoselectively preparing
REFERENCES:
Archiv Der Pharmazie; vol. 307, No. 8, pp. 653-655 1974.
Bernard Didier
Leon Patrick
Barts Samuel
Rhone-Poulenc Rorer S.A.
LandOfFree
Process for the preparation of N-carbonylarylimines useful in th does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of N-carbonylarylimines useful in th, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of N-carbonylarylimines useful in th will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-765926