Chemistry:Butanilicaine

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Butanilicaine
Butanilicaine.svg
Names
IUPAC name
N2-Butyl-N1-(2-chloro-6-methylphenyl)glycinamide
Systematic IUPAC name
2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
Properties
C13H19ClN2O
Molar mass 254.75576
Pharmacology
1=ATC code }} N01BB05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Butanilicaine is a local anesthetic. It is also known by the name Hostacaine.

Synthesis

Thieme Synthesis:[1][2] Patents:[3][4][5][6]

The amide formation between 2-Chloro-6-Methylaniline [87-63-8] (1) and Chloroacetyl chloride (2) gives 2-Chloro-n-(2-chloro-6-methylphenyl)acetamide [6307-67-1] (3). Alkylation with N-Butylamine (4) completed the synthesis of Butanilicaine (5).

References

  1. Haussler A, Ther L. [Chemical detection of hostacain]. Arzneimittelforschung. 1953;3(12):609-11.
  2. Epstein, Elias; Kaminsky, Daniel (1958). "N-(Substituted Aminoacyl)-chloroanilines". Journal of the American Chemical Society 80 (8): 1892–1895. doi:10.1021/ja01541a028.
  3. GB patent 726080 (1955 to Polymer Corp.)
  4. GB patent 759744 (1956 to Cilag)
  5. GB patent 782971 1957 to Hoechst AG.
  6. G. Ehrhart et al., U.S. Patent 2,912,460 (1959 to Hoechst).