S(Cl)([Cl:3])=O.[C:5]1([C:11]2[S:12][CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:25]=[CH:24][C:21]([CH2:22]O)=[CH:20][CH:19]=3)[N:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1CCCC1>C1(C)C=CC=CC=1>[Cl:3][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH2:16][C:14]2[N:15]=[C:11]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[S:12][CH:13]=2)=[CH:19][CH:20]=1A solution of thionyl chloride (1.5 ml) in toluene (5 ml) was added to a mixture of 4-(2-phenyl-4-thiazolylmethoxy)benzyl alcohol (4.35 g), tetrahydrofuran (50 ml) and toluene (50 ml) under ice-cooling, which was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate, and the solution was washed with saturated aqueous sodium bicarbonate solution, then with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain colorless crystals of 4-(4-chloromethylphenoxymethyl)-2-phenylthiazole (4.10 g, yield 89%). Melting point: 98–99° C.
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