N-Methylethylenediamine → N1-methyl-N1-(thiazol-5-yl)ethane-1,2-diamine
Reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][CH:3]=1.[CH3:7][NH:8][CH2:9][CH2:10][NH2:11]>C(O)(C)C.[Cu].[Cu]Cl>[CH3:7][N:8]([C:2]1[S:6][CH:5]=[N:4][CH:3]=1)[CH2:9][CH2:10][NH2:11]Participants
6
Procedure
37 mg (0.6 mmol) copper and 172 mg (1.7 mmol) copper(I) chloride were added to a solution of 1.15 ml (10.5 mmol) 5-bromothiazol and 5.6 ml (63.0 mmol) N-methyl-ethylene-diamine in isopropanol (6 ml). Heating was subsequently performed for 1 h to 70° C. Concentration was subsequently performed in a vacuum. The residue was received with brine (40 ml) and DCM (20 ml) and the phases were separated. The organic phase was dried over MgSO4, filtered and concentrated in a vacuum. CC (DCE/EtOH/conc. NH4OH 5:1:0.06) was performed with the residue, whereby 104 mg (0.7 mmol, 6%) N1-methyl-N1-(thiazol-5-yl)ethane-1,2-diamine was obtained.
Workup
- temperatureHeating
- concentrationConcentration
- customthe phases were separated
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in a vacuum
Sources & evidence
- ORD record
- ord-02051aa624294f4fbce10c78d3492fcc
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008304B2
Reaction notes
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