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ChemInform Abstract: Side Reaction of the Condensation of 5-Acetoxy-3-chloropentanone-2 and Thioformamide in the Synthesis of Vitamin B1.

✍ Scribed by M. M. LITVAK

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199832280

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✦ Synopsis

Side Reaction of the Condensation of 5-Acetoxy-3-chloropentanone-2 and Thioformamide in the Synthesis of Vitamin B 1 .

-It is shown for the first time that in the cyclocondensation of the title 3-chloropentanone (I) with thioformamide (II), a key step in the vitamin B 1 synthesis, besides the target thiazole (III) a "dithiazole" is formed. The reaction goes via a 3-(iminomethylthio)pentanone-2 intermediate which undergoes intra-or intermolecular cyclization to give the thiazole (III) and its dimer (IV), respectively.

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