|Systematic (IUPAC) name|
|CAS Registry Number|
|Molecular mass||323.38564 g/mol|
|(what is this?)|
Dimefline is a respiratory stimulant.
The Kostanecki acylation, which involves the esterification of ortho and acylphenol followed by aldol condensation of the resulting ketoester, provides a convenient entry to chromones. The subclass of 2-phenyl derivatives obtained by the use of benzoyl chloride is named flavones.
Reaction of o,p-dihydroxypropiophenone (1) with benzoyl chloride in the presence of sodium benzoate can be visualized as involving the initial formation of the ester (2). Internal condensation of the dicarbonyl derivative, which can proceed in only one direction, provides a new ring and results in a flavone (3). The remaining free phenolic group is then coverted to its methyl ether (4) by means of dimethyl sulfate. Reaction with formaldehyde in the presence of dry HCl (cf Blanc chloromethylation) serves to introduce a chloromethyl group (5). The displacement of chlorine by dimetylamine affords the respiratory stimulant dimefline (6).
- Da Re et al., Arzneim.-Forsch. 10, 800 (1960).
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