2-Furoyl chloride explained

2-Furoyl chloride is an acyl chloride of furan. It takes the form of a corrosive liquid, which is more irritating to the eyes than benzoyl chloride.[1] 2-Furoyl chloride is a useful pharmaceutical intermediate and is used in the synthesis of mometasone furoate, an antiinflammatory prodrug used in the treatment of skin disorders, hay fever and asthma.[2]

Synthesis

2-Furoyl chloride was prepared in 1924 by Gelissen by refluxing 2-furoic acid in excess thionyl chloride on a water bath.[1]

Applications

2-Furoyl chloride has no major applications but it has been used as a chemical intermediate in the synthesis of various pharmaceuticals; examples include mometasone furoate, fluticasone furoate,[3] diloxanide furoate,[4] Ceftiofur (Excenel),[5] mirfentanil,[6] quinfamide,[7] and diclofurime.[8]

See also

Notes and References

  1. H. Gelissen. Furfuroyl peroxide. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. 43. 59–66. 1924. van Roon. J. D..
  2. William Heggie, "Process for the preparation of mometasone furoate", US Patent 6,177,560 B1(2001)
  3. Dingjun Chu, "Method for preparation of Fluticasone furoate", CN 102558273 A 20120711 (2012)
  4. Wenli Zheng. Synthesis of diloxanide furoate. Zhongguo Yiyao Gongye Zazhi. 37 . 2. 77–78. 2006. Xue. Feiqun.
  5. Xuke Zhang, "Method for preparation of Ceftiofur", CN Patent 101,108,855 A (2008)
  6. Jerome R. Bagley. New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties. Journal of Medicinal Chemistry. 32 . 3. 663–71. 1989. Wynn. Richard. Rudo. Frieda. Doorley. Brian. Spencer. Kenneth. Spaulding. Theodore. 10.1021/jm00123a028. 2563773.
  7. Bailey. Denis M.. Mount. Eldridge M.. Siggins. James. Carlson. John A.. Yarinsky. Allen. Slighter. Ralph G.. 1979. 1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents. Journal of Medicinal Chemistry. en. 22. 5. 599–601. 10.1021/jm00191a031. 458814 . 0022-2623.
  8. DE2449205 idem Germaine Thuillier, Jacqueline Laforest, Pierre Bessin, (1977 to C.E.R.P.H.A. A French Society Organised Under The Laws Of France).

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