Chemistry:Butanilicaine

From HandWiki
Butanilicaine
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).