N-bromobutanimide → HCID 178467400, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-{trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexyl}methanesulfonamide (178 mg, 0.59 mmol) in DMF (4.0 mL) was added N-bromosuccinimide (104 mg, 0.585 mmol) and the reaction was heated at 50° C. for one hour. The reaction was then cooled to room temperature and another portion of N-bromosuccinimide (52 mg, 0.292 mmol) was added. The reaction was then heated at 50° C. for one hour. The solution was then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford N-{trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]cyclohexyl}methanesulfonamide. MS ESI calc'd. for C12H20N2O3S2 [M+H]+ 383, 385. found 383, 385. 1H NMR (500 MHz, DMSO-d6) δ 7.73 (s, 1H), 6.91 (d, J=7.4, 1H), 5.95 (s, 1H), 2.99-2.87 (m, 1H), 2.54 (s, 3H), 1.94-1.72 (m, 4H), 1.52 (t, J=11.9, 1H), 1.47-1.39 (m, 4H), 1.30-0.92 (m, 3H).

Provenance & Evidence