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Phenaglycodol









Phenaglycodol


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Phenaglycodol
Phenaglycodol.svg
Clinical data
ATC code
  • None
Identifiers
CAS Number
  • 79-93-6

PubChem CID
  • 6617
ChemSpider
  • 6365
ECHA InfoCard
100.001.124 Edit this at Wikidata
Chemical and physical data
Formula
C11H15ClO2
Molar mass 214.689 g/mol
3D model (JSmol)
  • Interactive image

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]




Contents






  • 1 Synthesis


    • 1.1 Notes




  • 2 See also


  • 3 References





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 "Novel trifluoromethyl derivatives of substituted diols" U.S. Patent 3,134,819 also.


See also[edit]



  • Metaglycodol

  • Fenpentadiol



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..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  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.















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