Development of Safe One-Pot Synthesis of N-1- and C-2-Substituted Benzimidazole via Reductive Cyclization of o-Nitroarylamine Using Na2S2O4

Oda, Shinichi; Shimizu, Hideki; Aoyama, Yasunori; Ueki, Tatsuo; Shimizu, Sumio; Osato, Hiroshi; Takeuchi, Yoshiyuki

doi:10.1021/op200251c.s001

op200251c_si_001.pdf (602.35 kB)

Development of Safe One-Pot Synthesis of N-1- and C-2-Substituted Benzimidazole via Reductive Cyclization of o-Nitroarylamine Using Na₂S₂O₄

journal contribution

posted on 2012-01-20, 00:00 authored by Shinichi Oda, Hideki Shimizu, Yasunori Aoyama, Tatsuo Ueki, Sumio Shimizu, Hiroshi Osato, Yoshiyuki Takeuchi

We report that the reductive cyclization of o-nitroarylamine with aldehyde using sodium dithionite (Na₂S₂O₄) could be accelerated by addition of H₂O, which made it possible to control the heat release of the reaction by semibatch-type operation. Safety evaluation was performed using DSC, ARSST, in situ IR analysis, and Multimax.