Boron tribromide → HCID 57725645, compound
Reaction equation
[CH:1]1([C@@H:7]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19]C)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C@@H:7]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)—N-(1-cyclohexylethyl)-6-methoxybenzo[d]thiazol-2-amine (3.39 g, 10 mmol) in 30 mL of DCM was added 1 M boron tribromide in DCM (20 mL, 20 mmol) slowly at 0° C. The reaction solution was stirred at 0° C. for 20 min and then at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc (400 mL) and water (90 mL) and stirred at room temperature for 10 min. To the mixture was added excess solid NaHCO3 until basic. Stirring was continued at room temperature for 1 hour. The separated aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed water (50 mL), saturated NaCl solution (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography with EtOAc/hexanes (3/7) provided the title compound as a solid (2.0 grams). ES/MS m/z 277.1 (MH+).