Hydrogen Bromide → HCID 53408113, Verbindung

t-Butylnitrite (50%, 2.3 mL, 17.22 mmol) was added dropwise to a degassed solution of CuBr2 (1.64 g, 7.35 mmol) in acetone (30 mL) at 0° C. under N2. The mixture was stirred at ambient temperature for 90 min, then charged with a solution of 3-(1-methylethyl)-1,2,4-thiadiazol-5-amine (1 g, 7 mmol) in acetone (7 mL), and stirred at ambient temperature for 1 h. The mixture was cooled to 0° C., and was charged dropwise with 48% HBr (1.8 mL, 4.65 mmol). The mixture was stirred at 0° C. for 30 min, and then brought to ambient temperature. The mixture was charged with water (100 mL) and CH2Cl2 (75 mL), then stirred at ambient temperature for 10 min. The organics were separated, dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 15% EtOAc/hexane to give 1.07 g (74%) of 5-bromo-3-(1-methylethyl)-1,2,4-thiadiazole as a golden oil. 1H NMR (400 MHz, CDCl3): δ 3.29 (septet, 1H, J=6.9 Hz), 1.37 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 207/209 (M+H).

1. stirringstirred at ambient temperature for 1 h
2. temperatureThe mixture was cooled to 0° C.
3. stirringThe mixture was stirred at 0° C. for 30 min
4. custombrought to ambient temperature
5. stirringstirred at ambient temperature for 10 min
6. customThe organics were separated
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthe filtrate was concentrated
10. customThe crude product was purified by chromatography on a silica gel column

ORD-Eintrag

ord-4c84de87bb4045b6b011e267a03697fe

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08101634B2