Synthesis of alpha-chloroaldoxime O-methanesulfonates and their use in the synthesis of functionalized benzimidazoles.
Three different alpha-chloroaldoxime O-methanesulfonates were synthesized to investigate their chemical properties. The compounds were found to be stable and were able to be stored at ambient temperature without any precautions. The reactions with anilines were investigated, and it was found that an additive is required to activate the sulfonate. TMEDA was found to be the most efficient additive, and various benzimidazoles were synthesized through the reaction.
Yamamoto
Yuhei
Y
Process Research, Preclinical Development, Banyu Pharmaceutical Co., Ltd., 3 Okubo, Tsukuba, Ibaraki, 300-2611, Japan. yuhei_yamamoto@merck.com
Mizuno
Hiroo
H
Tsuritani
Takayuki
T
Mase
Toshiaki
T
D000814:Aniline Compounds / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis / Q000737:chemistry; D008698:Mesylates / Q000138:chemical synthesis / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry*
D000814:Aniline Compounds; D001562:Benzimidazoles; D006843:Hydrocarbons, Chlorinated; D008698:Mesylates; D010091:Oximes