Thionyl Chloride → 4-Tert-butyl-2-[5-(3-chloropropyl)benzofuran-2-yl]thiazole
Reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21]O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:25])=O>ClCCl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][Cl:25])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propanol (0.40 g) and thionyl chloride (0.4 ml) in dichloromethane (5 ml) was stirred under reflux for 5 hours. After being cooled to room temperature, the solution was concentrated under reduced pressure. The resulting residue -was partitioned between aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a 4-tert-butyl-2-[5-(3-chloropropyl)benzofuran-2-yl]thiazole (0.28 g).