Reaction #44096

Reaction equation

Dichloromethane

1-[3-(2-Hydroxyethyl)phenyl]-2-imidazolidinone

Triethylamine

methanesulfonyl chloride

→

title compound

Yield 70.0%

2-[3-(2-Oxo-1-imidazolidinyl)phenyl]ethyl methanesulfonate

Yield 70.0%

Solvents

Methyl-t-butyl ether

DMF

Conditions

Workup

1. 1
   Otherwas obtained
2. 2
   TemperatureThe mixture was cooled to 20° C.
3. 3
   Washthe organic layer was washed with brine/water (1:1) (5 vol)
4. 4
   ConcentrationThe organic phase was concentrated to 1 vol, and methanol
5. 5
   workup.ADDITIONwas added (4 vol)
6. 6
   workup.DISSOLUTIONif complete dissolution
7. 7
   Otherwas not obtained
8. 8
   Temperaturethe mixture was heated to 35° C. in order
9. 9
   workup.DISSOLUTIONto dissolve the solid
10. 10
    workup.WAITthe suspension was left
11. 11
    workup.WAITto stand for 18 hours at room temperature
12. 12
    FiltrationThe suspension was filtered
13. 13
    Washthe filter-cake was washed with methyl-t-butyl ether (2 vol)
14. 14
    OtherThe solid was dried at 40° C. for 18 hours

Procedure

1-[3-(2-Hydroxyethyl)phenyl]-2-imidazolidinone was suspended in DMF (4 vol) and heated to 35° C. until a clear solution was obtained. Triethylamine (1 vol) was added dropwise at 30° C. over 15 minutes. The mixture was cooled to 20° C. and methanesulfonyl chloride (0.46 vol) was added 30 mins. The resulting suspension was stirred at 20° C. for 15 minutes. Dichloromethane (10 vol) was added, and the organic layer was washed with brine/water (1:1) (5 vol), and then water (3×5 vol). The organic phase was concentrated to 1 vol, and methanol was added (4 vol), if complete dissolution was not obtained, the mixture was heated to 35° C. in order to dissolve the solid. Methyl-t-butyl ether (10 vol) was added and the suspension was left to stand for 18 hours at room temperature. The suspension was filtered; the filter-cake was washed with methyl-t-butyl ether (2 vol). The solid was dried at 40° C. for 18 hours to give the title compound (70% th).

Source