Hydrochloric Acid → 1-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclohexanol

A mixture of 3,3-dimethylbutanal (3.0 mL, 24 mmol), 1-(aminomethyl)cyclohexanol, hydrochloric acid (3.6 g, 22 mmol), triethylamine (3.0 mL, 22 mmol), and 3 g of 4 Å molecular sieves (8-12 mesh beads) in acetonitrile (25 mL) was stirred at ambient temperature for 20 h. The material was filtered through Celite® with acetonitrile (additional 20 mL) then potassium thiocyanate (2.8 g, 29 mmol) was added and the mixture was warmed to 50° C. Iodine (5.5 g, 22 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 50 mL of 20% aqueous sodium metabisulfite for 1 h then 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 which was carried on without further purification. MS (DCI/NH3) m/z 269 (M+H)+.

1. filtrationThe material was filtered through Celite® with acetonitrile (additional 20 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-Eintrag

ord-1046fa42e87f4385b89530988cace2fd

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07875640B2