Phenaglycodol

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Phenaglycodol
Phenaglycodol.svg
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
ECHA InfoCard 100.001.124 Edit this at Wikidata
Chemical and physical data
Formula C11H15ClO2
Molar mass 214.689 g/mol
3D model (JSmol)

Phenaglycodol (brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran)[1] is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties.[2][3] It is related structurally and pharmacologically to meprobamate, though it is not a carbamate.[4][5]

Synthesis[edit]

Jack Mills "2-chlorophenyl-3-methyl-2, 3-butanediols" U.S. Patent 2,812,363 (1957 to Eli Lilly Co.).

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.

Notes[edit]

See also[edit]

References[edit]

  1. ^ Earl Usdin; Daniel H. Efron; National Institute of Mental Health (U.S.) (1972). Psychotropic drugs and related compounds. National Institute of Mental Health; [for sale by the Supt. of Docs., U.S. Govt. Print. Off., Washington. 
  2. ^ Julius Vida (19 July 2013). Anticonvulsants. Elsevier. pp. 578–. ISBN 978-0-323-14395-0. 
  3. ^ Lester M. Haddad; James F. Winchester (1983). Clinical Management of Poisoning and Drug Overdose. Saunders. ISBN 978-0-7216-4447-9. 
  4. ^ Victor Alexander Drill (1958). Pharmacology in Medicine: A Collaborative Textbook. McGraw-Hill. 
  5. ^ Harry Beckman (1961). Pharmacology; the nature, action and use of drugs. Saunders.