Iodine → 5-tert-butyl-3-propylthiazol-2(3H)-imine

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Reaction Steps

A mixture of 3,3-dimethylbutanal (5 mL, 40 mmol), propan-1-amine (3.0 mL, 36 mmol), and 4 g of 4 Å molecular sieves (8-12 mesh beads) in acetonitrile (40 mL) was stirred at ambient temperature for 16 h. The material was filtered through Celite® with acetonitrile (additional 25 mL) then potassium thiocyanate (4.7 g, 48 mmol) was added and the mixture was warmed to 50° C. Iodine (18 g, 72 mmol) was added and the mixture was stirred at 50° C. for 16 h then was cooled to ambient temperature. The mixture was then stirred with 75 mL of 20% aqueous sodium metabisulfite for 1 h. The layers were separated and the aqueous layer was extracted with 3×10 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the title compound (7.1 g, 36 mmol, 99% yield) which was carried on without further purification. MS (DCI/NH3) m/z 199 (M+H)+.

Provenance & Evidence