A Convergent Continuous Multistep Process for the Preparation of C4-Oxime-Substituted Thiazoles
- Edouard Godineau *†
- Claudio Battilocchio †‡
- Matthias Lehmann †
- Steven V. Ley †
- Ricardo Labes ‡
- Letitia Birnoschi ‡
- Srinivas Subramanian §
- C.S Prasanna §
- Amol Gorde §
- Mahesh Kalbagh §
- Vivek Khade §
- Anton Scherrer †
- Anthony C. O’Sullivan †
- † Syngenta Crop Protection, Process Research, Schaffhauserstrasse 101, CH-4332, Switzerland
- ‡ Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, UK
- § Syngenta Research and Technology Centre, Santa Monica Works, Corlim, Goa India, 403110Read the publication that featured this abstract
We report a strategy designed for the rapid and convergent assembly of C4-oxime substituted thiazoles. Our approach relied on 3-bromo-2-oxopropanal O-methyl oxime 7 as a key building block. A three-step sequence to 7 was designed, which, for safety concerns, could only be operated in batch mode on limited scales (≪100 g). We describe herein how we addressed such a limitation, by designing a multistep continuous synthesis of this intermediate and further demonstrate the advantages of flow reactor configuration upon scaling up.
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