Triethylamine → 2-(2-Oxoimidazolidin-1-yl)ethyl methanesulfonate

HRID 2274777Notes

Reaction equation

HRID 2274777 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].CCN(CC)CC.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 77290Hydroxyethyl imidazolidinone

Product 1

HCID 190455732-(2-Oxoimidazolidin-1-yl)ethyl methanesulfonateYield 44.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-hydroxyethyl)imidazolidin-2-one (100 mg; 0.77 mmol) and Et3N (81 mg; 0.80 mmol) in dry DCM (10 mL) was added MsCl (137 mg; 1.20 mmol) under nitrogen. The reaction mixture was stirred overnight, diluted with DCM (20 mL), washed with saturated aqueous Na2CO3, dried over anhydrous Na2SO4, concentrated to afford 72 mg (44%) of the title compound as a yellow oil, which was used directly without further purification.

Workup

  1. washwashed with saturated aqueous Na2CO3
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e1d36cef2f4c45e38ac354efd442eef4
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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