Triethylamine → 2-Thiazolemethanol, 4-(2-chlorophenyl)-, 2-methanesulfonate

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Reaction Conditions

Reaction Steps

(4-(2-chlorophenyl)thiazol-2-yl)methanol 3 (0.41 g, 1.82 mmol) is dissolved in dichloromethane (25 mL). Triethylamine (0.50 mL, 3.56 mmol) is added and the solution is cooled to 0° C. Methanesulfonyl chloride (0.17 mL, 2.19 mmol) is added dropwise to the cooled solution, with stirring. The bath is removed and the mixture is stirred at room temperature for 3 h. Addition of water, extraction with DCM, drying over MgSO4 and concentration yielded (4-(2-chlorophenyl)thiazol-2-yl)methyl methanesulfonate 4 as an oil: 1H-NMR (400 MHz, CDCl3) δ=7.93 (s, 1H) 7.90 (dd, J=1.9, 7.7 Hz, 1H), 7.48 (dd, J=1.4, 7.7 Hz, 1H), 7.36 (ddd, J=1.4, 7.4, 7.6 Hz, 1H), 7.30 (ddd, J=1.9, 7.7, 7.5 Hz, 1H), 5.56 (s, 2H), 3.13 (s, 3H). MS calcd. for C11H11ClNO3S2 (M+H+) 304.0. found 303.9.

Provenance & Evidence