Reaktion #165728

Reaktionsgleichung

iodine

3,3-dimethylbutanal

(R)-(tetrahydrofuran-2-yl)methanamine

sodium metabisulfite

potassium thiocyanate

→

title compound

Ausbeute 50.0%

5-tert-butyl-3-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-imine hydroiodide

Ausbeute 50.0%

Lösungsmittel

acetonitrile

ethyl acetate

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigewas adjusted to 50° C.
3. 3
   workup.STIRRINGthe mixture was stirred until the solids
4. 4
   workup.DISSOLUTIONwere dissolved
5. 5
   workup.STIRRINGstirred at 50° C. for 24 hr
6. 6
   TemperaturThe reaction mixture was cooled
7. 7
   workup.STIRRINGstirred for 30 min
8. 8
   SonstigeThe organic layer was separated
9. 9
   WaschenThe aqueous layer was washed with dichloromethane (3×40 mL)
10. 10
    TrocknenThe combined organic extracts were dried with sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated
13. 13
    Sonstigeto obtain the crude product as a yellow solid
14. 14
    workup.ADDITIONwas added
15. 15
    Temperaturthe mixture was warmed to 40° C.
16. 16
    Sonstigesonicated
17. 17
    workup.WAITleft in the refrigerator overnight
18. 18
    SonstigeThe solid was collected
19. 19
    Waschenwashed with cold ethyl acetate

Vorschrift

To a solution of 3,3-dimethylbutanal (9.90 g, 99 mmol) in acetonitrile (60 mL) were added molecular sieves (8 g) and (R)-(tetrahydrofuran-2-yl)methanamine (10 g, 99 mmol). The reaction mixture was stirred at room temperature for 24 hr and then filtered. To the filtrate was added potassium thiocyanate (12.78 g, 131 mmol). The temperature was adjusted to 50° C. and the mixture was stirred until the solids were dissolved. Then, iodine (25.09 g, 99 mmol) was added to the mixture and stirred at 50° C. for 24 hr. The reaction mixture was cooled, and to the mixture was added sodium metabisulfite (20%, 100 mL) and stirred for 30 min. The organic layer was separated. The aqueous layer was washed with dichloromethane (3×40 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated to obtain the crude product as a yellow solid. The residue was taken into dichloromethane (20 mL) and ethyl acetate (80 mL) was added, the mixture was warmed to 40° C., sonicated, and left in the refrigerator overnight. The solid was collected and washed with cold ethyl acetate to obtain the title compound as a white solid (18.2 g, 50%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.27 (s, 9H) 1.48-1.61 (m, 1H) 1.78-1.93 (m, 2H) 1.94-2.07 (m, 1H) 3.62-3.71 (m, 1H) 3.76-3.84 (m, 1H) 3.92-4.08 (m, 2H) 4.11-4.20 (m, 1H) 7.19 (s, 1H) 9.39 (s, 2H); MS (DCI/NH3); m/z 241 (M+H)+.

Quelle