Triethylamine → 3-[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one

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Reaction Conditions

Reaction Steps

2-{[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol (0.80 g, 2.4 mmol), prepared in the previous step, was dissolved in methylene chloride (20 mL), triethylamine (3.3 mL, 24 mmol) was added, and the mixture was cooled to 0° C. Triphosgene (1.8 g, 6.1 mmol) was added and the mixture was stirred for 2.5 h. The mixture was then diluted with methylene chloride and washed with 2N HCl, saturated NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (7.5% acetone/hexane) afforded the title compound (730 mg, 86%). Analytical HPLC: purity 100% at 210-370 nm, 11.0 min; 100% at 246 nm, 11.0 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence