title: Synthesis of alpha-chloroaldoxime O-methanesulfonates and their use in the synthesis of functionalized benzimidazoles.
abstract: 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.
authors.affiliation: Process Research, Preclinical Development, Banyu Pharmaceutical Co., Ltd., 3 Okubo, Tsukuba, Ibaraki, 300-2611, Japan. yuhei_yamamoto@merck.com
authors.forename: Yuhei
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Hiroo
authors.initials: H
authors.lastname: Mizuno
authors.forename: Takayuki
authors.initials: T
authors.lastname: Tsuritani
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Mase
mesh_terms: 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*
chemical_list: D000814:Aniline Compounds; D001562:Benzimidazoles; D006843:Hydrocarbons, Chlorinated; D008698:Mesylates; D010091:Oximes