Iodine → 2-(5-tert-butyl-2-iminothiazol-3(2H)-yl)ethanesulfonamide

A mixture of 3,3-dimethylbutanal (2.15 mL, 17.1 mmol), triethylamine (2.2 mL, 15.6 mmol), 2-aminoethanesulfonamide-hydrochloric acid (2.5 g, 15.6 mmol), and 4 g of 4 Å molecular sieves (8-12 mesh beads) in acetonitrile (40 mL) was stirred at ambient temperature for 20 h. This material was filtered through Celite with acetonitrile (additional 25 mL) then potassium thiocyanate (2.0 g, 20.7 mmol) was added and the mixture was warmed to 50° C. Iodine (3.95 g, 15.6 mmol) was added and the mixture was stirred at 50° C. for 16 h then was cooled to ambient temperature. The mixture was stirred with 50 mL of 20% aqueous sodium metabisulfite for 1 h then the layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the crude title compound (0.5 g, 1.9 mmol, 12.2% yield) which was carried on without further purification. MS (DCI/NH3) m/z 264 (M+H)+.

1. filtrationThis 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 CH2Cl2 (3×10 mL)
7. dry with materialThe combined organics were dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-9872298f143740bf901855200d9fc97e

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058293B2