Chlorosuccinimide → HCID 86618577, compound

Participants

Reaction Steps

A solution of N-chlorosuccinimide (975.0 mg, 7.30 mmol) in 50 mL of methylene chloride was added under nitrogen at room temperature dropwise over 45 min to a solution of (2S)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}butan-1-ol (2.1611 g, 6.60 mmol), prepared in step 1 of Example 7, in 50 mL of methylene chloride. After the addition, the reaction was stirred at room temperature for 3 h. The reaction was poured directly onto a column of silica gel (230-400 mesh). Elution of the column with 5% ethyl acetate-methylene chloride to 15% ethyl acetate-methylene chloride gave (2S)-2-{[4-(4-bromophenyl)-5-chloro-1,3-thiazol-2-yl]amino}butan-1-ol (1.5371 g, 64%) as a yellow foam, MS (ES) m/z 358.8 [M+H]+.

Provenance & Evidence