Iodine → 5-tert-Butyl-3-[(S)-1-(tetrahydro-furan-2-yl)methyl]-3H-thiazol-2-ylideneamine

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To a solution of 3,3-dimethylbutanal (Aldrich) (1.52 mL, 12.1 mmol) and (S)-(tetrahydrofuran-2-yl)methanamine (Aldrich) (1.00 g, 9.89 mmol) in 12 mL of acetonitrile was added 1.20 g of molecular sieves (4 Å beads, 8-12 mesh). The mixture was stirred for 12 h at 22° C. The mixture was filtered and to the filtrate was added potassium thiocyanate (1.42 g, 14.6 mmol). The temperature was adjusted at 50° C. and the mixture was stirred until all solids were dissolved, then iodine (5.58 g, 22.0 mmol) was added. The reaction was stirred at 50° C. for 12 h. The reaction was cooled to room temperature and diluted with EtOAc. The solution was washed with a solution of sodium bisulfate. The aqueous layers was brought to pH=9 by adding aq. NaOH (25%) and extracted with EtOAc. The organic extracts were combined, dried with sodium sulfate, filtered, and concentrated. The residue was crystallized from EtOAc/Hexane to give the title compound. MS (ESI−) m/z 241 (M+H)+.

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