2-[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]acetonitrile → 2-(2-(4-Chlorophenyl)thiazol-4-yl)ethanamine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][C:14]#[N:15])[N:12]=2)=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH2:15])[N:12]=2)=[CH:6][CH:7]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Borane dimethyl sulfide complex (0.24 mL, 2.5 mmol) was added to a solution of 2-(2-(4-chlorophenyl)thiazol-4-yl)acetonitrile (150 mg, 0.63 mmol) in dry THF (15 mL) at room temperature. The reaction mixture was refluxed for 0.5 h and then quenched carefully with methanol. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2-(2-(4-chlorophenyl)thiazol-4-yl)ethanamine (150 mg, crude) which was used as such for the next step.