2-Chloroethyl isocyanate → 1-(Prop-2-yn-1-yl)imidazolidin-2-one

HRID 483631Notes

Reaction equation

HRID 483631 reaction equation
Cl[CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH2:7]([NH2:10])[C:8]#[CH:9]>C1COCC1>[CH2:7]([N:10]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6])[C:8]#[CH:9]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 239041Propargylamine

Product 1

HCID 156696571-(Prop-2-yn-1-yl)imidazolidin-2-oneYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chloroethyl isocyanate (12.2 g, 0.11 mol) was added at 0° C. to a stirred solution of propargylamine (6.6 g, 0.12 mol) in THF (200 mL). The solution was allowed to warm to room temperature and sodium hydride (5.5 g of 50% in oil, washed with ether to remove the oil) was added. The reaction was quenched with acetic acid (6.0 mL), the THF was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The ethyl acetate was evaporated and the residual solid was crystallized from ethyl acetate: Skellysolve B to give 11.1 g of 1-(2-propynyl)-2-imidazolidinone, m.p. 110°-115° C.

Workup

  1. washsodium hydride (5.5 g of 50% in oil, washed with ether
  2. customto remove the oil)
  3. additionwas added
  4. customThe reaction was quenched with acetic acid (6.0 mL)
  5. customthe THF was removed under reduced pressure
  6. customthe residue was partitioned between ethyl acetate and water
  7. customThe ethyl acetate was evaporated
  8. customthe residual solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-142f28b99b884f1083d8c83483935fa6
Source dataset
uspto-grants-1993_07
Patent number
US05225567

Reaction notes

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