m-Chloroperbenzoic acid → HCID 25050367, compound

Participants

Reaction Conditions

Reaction Steps

1-(3,4-Dichlorobenzyl)-3-(4-((2-(methylthio)ethoxy)methyl)thiazol-2-yl)urea (Example 26) (0.98 mmol, 0.4 g) was dissolved in CHCl3 (10 mL) and cooled to 0° C. 3-Chloroperbenzoic acid (1 eq, 0.98 mmol, 0.17 g) was added and the mixture was stirred at room temperature overnight. LC-MS indicated the product was a mixture of sulfoxide and sulfone. Sodium bicarbonate (saturated, 10 mL) was added and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated to give an oil. Purification by preparative HPLC yielded 0.048 g of the title compound as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.49-7.45 (m, 2H), 7.25 (m, 1H), 6.85 (s, 1H), 4.87 (s, 2H), 4.45 (s, 2H), 3.86 (m, 2H), 3.11-2.91 (m, 2H), 2.65 (s, 3H).

Provenance & Evidence