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

Temperatur

22 °C

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)+.

1. filtrationThe mixture was filtered and to the filtrate
2. customwas adjusted at 50° C.
3. stirringthe mixture was stirred until all solids
4. dissolutionwere dissolved
5. stirringThe reaction was stirred at 50° C. for 12 h
6. temperatureThe reaction was cooled to room temperature
7. washThe solution was washed with a solution of sodium bisulfate
8. additionby adding aq. NaOH (25%)
9. extractionextracted with EtOAc
10. dry with materialdried with sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was crystallized from EtOAc/Hexane

ORD-Eintrag

ord-e4e2da3c78ce45cab41a5cac1c29effa

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841334B2