Ethylenediamine → N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]ethane-1,2-diamine
Reaktionsgleichung
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[N:6]=1.[CH2:14]([NH2:17])[CH2:15][NH2:16].C([O-])(O)=O.[Na+]>>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([NH:16][CH2:15][CH2:14][NH2:17])[S:3][CH:4]=2)=[CH:8][CH:9]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
2-Bromo-4-(4-bromophenyl)-1,3-thiazole (2.0 g, 6.2 mmol), prepared in step 2 of Example 1, was dissolved in ethylenediamine (10.0 mL, 185 mmol) and heated to 130° C. for 2 h. The mixture was cooled and poured into saturated NaHCO3 and extracted with ether. The ether extracts were combined and washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]ethane-1,2-diamine (1.8 g, 97%) as a yellow solid. HRMS: calcd for C11H12BrN3S+H+, 298.00080; found (ESI, [M+H]+), 298.0012. Analytical HPLC: retention time 7.0 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40 C 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.