Triethylamine → Thiazole, 5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-

Participants

Reaction Steps

To an ice-cooled solution of [2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (1.556 g, 6.0 mmol) and Et3N (1.67 ml, 12.0 mmol) in CH2Cl2 (14 ml) was slowly added methanesulfonyl chloride (0.75 ml, 9.6 mmol). After 2 h at 0° C. more Et3N (0.17 ml, 1.2 mmol) and methanesulfonyl chloride (0.07 ml, 0.96 mmol) were added. The reaction was kept for 16 h at 0° C. and 4 h at RT until the reaction was completed by TLC (n-heptane/EtOAc 4:1). The reaction was then partitioned between Et2O (3×)/aqueous saturated NaHCO3. The organic phases were washed once with aqueous 10% KHSO4. and aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 1.58 g (95%) of 5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole as a light yellow solid, MS: 277 (M, 1Cl), MP: 55-57° C.

Provenance & Evidence