Generation of hazardous methyl azide and its application to synthesis of a key-intermediate of picarbutrazox, a new potent pesticide in flow. Issue 23 (1st December 2017)

• Record Type: Journal Article
• Authors: Ichinari, Daisuke; Nagaki, Aiichiro; Yoshida, Jun-ichi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 25:Issue 23(2017)
• Page Start: 6224
• Page End: 6228
• Publication Date: 2017-12-01
• Subjects: Flow synthesis -- Methyl azide; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2017.07.005
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: Generation and reactions of methyl azide (MeN3 ) were successfully performed by using a flow reactor system, demonstrating that the flow method serves as a safe method for handling hazardous explosive methyl azide. The reaction of NaN3 and Me2 SO4 in a flow reactor gave a MeN3 solution, which was used for Huisgen reaction with benzoyl cyanide in a flow reactor after minimal washing. The resulting 1-methyl-5-benzoyltetrazole serves as a key intermediate of picarbutrazox (IX), a new potent pesticide.