Water → N1-ethyl-N1-(thiazol-2-yl)ethane-1,2-diamine
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Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH2:7]([NH:9][CH2:10][CH2:11][NH2:12])[CH3:8].O>C(O)(C)C.[Cu].[Cu]Cl>[CH2:7]([N:9]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH2:10][CH2:11][NH2:12])[CH3:8]Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH2:7]([NH:9][CH2:10][CH2:11][NH2:12])[CH3:8].O>C(O)(C)C.[Cu].[Cu]Cl>[CH2:7]([N:9]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH2:10][CH2:11][NH2:12])[CH3:8]47 mg (0.74 mmol) of copper and 225 mg (2.27 mmol) of copper(I) chloride were added to a solution of 1.35 g (15.0 mmol) of 2-bromothiazole and 9.48 ml (90.0 mmol) of N-ethylethylenediamine in isopropanol (7.5 ml). The mixture was then heated to 70° C. for 1 h. After cooling to RT, the reaction solution was poured into water and extracted with EA. The organic phase was dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (1.2 mmol, 8%) of N1-ethyl-N1-(thiazol-2-yl)ethane-1,2-diamine were obtained by carrying out CC twice (i. DCE/EtOH 5:1; ii. DCE/EtOH/conc. aq. NH4OH soln. 5:1:0.06) with the residue.
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