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

HRID 734536Notes

Reaction equation

HRID 734536 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].ClCCl>CN(C=O)C.COC(C)(C)C>[CH3:23][S:24]([O:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH:5]=1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 574442961-[3-(2-Hydroxyethyl)phenyl]-2-imidazolidinone

Product 1

HCID 574442972-[3-(2-Oxo-1-imidazolidinyl)phenyl]ethyl methanesulfonateYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
35 °C

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).

Workup

  1. customwas obtained
  2. temperatureThe mixture was cooled to 20° C.
  3. washthe organic layer was washed with brine/water (1:1) (5 vol)
  4. concentrationThe organic phase was concentrated to 1 vol, and methanol
  5. additionwas added (4 vol)
  6. dissolutionif complete dissolution
  7. customwas not obtained
  8. temperaturethe mixture was heated to 35° C. in order
  9. dissolutionto dissolve the solid
  10. waitthe suspension was left
  11. waitto stand for 18 hours at room temperature
  12. filtrationThe suspension was filtered
  13. washthe filter-cake was washed with methyl-t-butyl ether (2 vol)
  14. customThe solid was dried at 40° C. for 18 hours

Sources & evidence

ORD record
ord-d35d516e2a5540e0b537ca4ed99e5bc0
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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