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

HRID 15819Notes

Reaction equation

HRID 15819 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]>C(#N)C.C(OCC)(=O)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

6

Reactant 3

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

Product 1

HCID 574442972-[3-(2-Oxo-1-imidazolidinyl)phenyl]ethyl methanesulfonateYield 90%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Alternatively, 1-[3-(2-hydroxyethyl)phenyl]-2-imidazolidinone was suspended in acetonitrile (5 vol) at room temperature and under nitrogen. Triethylamine (1 vol) was added dropwise over 15 minutes. The mixture was cooled to 0° C. and methanesulfonyl chloride (0.73 vol) was added over 30 minutes. The reaction mixture was stirred at room temperature for 2 hours, then diluted with ethyl acetate (10 vol). The mixture was washed with a saturated solution of ammonium chloride (2×3 vol), followed by water-brine 1:1 (2×3 vol). The organic phase was concentrated to 5 vol, ethyl acetate (5 vol) was added and the solution was evaporated to dryness, yielding the title compound as a cream-coloured solid (yield: 90% th).

Workup

  1. washThe mixture was washed with a saturated solution of ammonium chloride (2×3 vol)
  2. concentrationThe organic phase was concentrated to 5 vol, ethyl acetate (5 vol)
  3. additionwas added
  4. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-8292b4c04b144d2f893018d610388da4
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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