反应详情

To a solution of 15.0 g (0.074 mol) of 2-[4-(1H-imidazol-1-yl)phenoxy]ethanol in 100 mL of N,N-dimethylformamide (DMF) was added 3.8 g (0.1 mol) of sodium hydride (60% oil dispersion) portionwise and the mixture was stirred at ambient temperature for 3 h. To this mixture was added 13.7 g (0.1 mol) of dimethylsulfamoyl chloride and the mixture was stirred at ambient temperature overnight. The reaction mixture was poured into 1.2 L of water and its pH was adjusted to 10 with sodium carbonate. The mixture was extracted with three 400-mL portions of ethyl acetate. The combined organic layers were washed twice with 400-mL portions of water, dried (MgSO4), and the solvent was evaporated under reduced pressure to give a viscous residue. The residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A; PrepPAK 500 silica; ethyl acetate; flow rate 150 mL/min). Fractions containing the product were combined and the solvent was evaporated under reduced pressure to give the title compound, a viscous oil. The oil was converted to the hydrochloride (2-propanol; ethereal HCl) and the white solid was collected by filtration to yield 5.9 g (26%), mp 120°-123° C.

1. stirringthe mixture was stirred at ambient temperature overnight
2. extractionThe mixture was extracted with three 400-mL portions of ethyl acetate
3. washThe combined organic layers were washed twice with 400-mL portions of water
4. dry with materialdried (MgSO4)
5. customthe solvent was evaporated under reduced pressure
6. customto give a viscous residue
7. customThe residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A; PrepPAK 500 silica; ethyl acetate; flow rate 150 mL/min)
8. additionFractions containing the product
9. customthe solvent was evaporated under reduced pressure