Thionyl Chloride → 2-(Chloromethyl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH2:14]O)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:20])=O>O1CCCC1>[Cl:20][CH2:14][C:11]1[S:12][CH:13]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=2)[N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The compound (4.14 g) obtained in Example 103a was dissolved in tetrahydrofuran (100 mL), and thionyl chloride (3.5 mL) was added. The reaction mixture was stirred at room temperature for 24 hr, and heated under reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (3.19 g) as a colorless solid.