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

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)+.

1. filtrationThe material was filtered through Celite® with acetonitrile (additional 25 mL)
2. temperaturethe mixture was warmed to 50° C
3. stirringthe mixture was stirred at 50° C. for 16 h
4. temperaturethen was cooled to ambient temperature
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with 3×10 mL CH2Cl2
7. dry with materialThe combined organics were dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-d1d302868d534797ae58859af84e9c2b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865753B2