ATC code None PubChem CID 6617 Formula C11H15ClO2 Molar mass 214.689 g/mol | CAS Number 79-93-6 ECHA InfoCard 100.001.124 3D model (Jmol) Interactive image ChemSpider ID 6365 | |
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Phenaglycodol (INN, BAN; brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran) is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties. It is related structurally and pharmacologically to meprobamate, though it is not a carbamate.
Contents
Synthesis
p-Chloroacetophenone and NaCN are reacted together to give the corresponding cyanohydrin (cf Strecker synthesis). The cyano group is then hydrated in acid to the corresponding amide, thus p-chloroatrolactamide (4) is formed. The amide group is then further hydrolyzed with a 2nd equivalent of water in concentrated lye to p-chloroatrolactic acid (5); this is then esterified to Ethyl p-chloroatrolactate (6). Finally, nucleophilic addition a couple of equivalents of MeMgI are added to the ester give Phenaglycodol (7) crystals.