Propargyl bromide → 1-Methyl-3-(2-propynyl)-2-imidazolidinone

HRID 846647Notes

Reaction equation

HRID 846647 reaction equation
[H-].[K+].[CH3:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[CH2:10](Br)[C:11]#[CH:12]>C1COCC1.C1(C)C=CC=CC=1>[CH3:3][N:4]1[CH2:8][CH2:7][N:6]([CH2:12][C:11]#[CH:10])[C:5]1=[O:9]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 82127Potassium hydrideHCID 5676001-Methylimidazolidin-2-one

Product 1

HCID 113555131-Methyl-3-(2-propynyl)-2-imidazolidinone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of potassium hydride (10.44 g of a 35% by wt suspension in mineral oil, washed with ether to remove oil, 0.09 mol) in dry THF (50 mL) was added dropwise, with cooling, to a stirred solution of 1-methyl-2-imidazolidinone (7.6 g, 0.076 mol) in dry THF (150 mL). After warming to room temperature and stirring for 20 min, the reaction was cooled again and propargyl bromide (13.54 g of an 80% solution in toluene, 0.09 mol) was added dropwise. The reaction was then allowed to slowly warm to room temperature and was stirred for 0.5 hr. The reaction was quenched with methanol and water and the solvents were removed under reduced pressure. The residual oil was partitioned between ethyl acetate and water; evaporation of the organic phase gave 10.65 g crude product. The compound was purified by chromatography on silica gel in chloroform to get 4.51 g of crystalline product.

Workup

  1. washwashed with ether
  2. customto remove oil, 0.09 mol) in dry THF (50 mL)
  3. additionwas added dropwise
  4. temperaturethe reaction was cooled again
  5. temperatureto slowly warm to room temperature
  6. stirringwas stirred for 0.5 hr
  7. customThe reaction was quenched with methanol and water
  8. customthe solvents were removed under reduced pressure
  9. customThe residual oil was partitioned between ethyl acetate and water
  10. customevaporation of the organic phase
  11. customgave 10.65 g crude product
  12. customThe compound was purified by chromatography on silica gel in chloroform

Sources & evidence

ORD record
ord-6f1c003a593f4327a321a486eb18a7c5
Source dataset
uspto-grants-1992_08
Patent number
US05137905

Reaction notes

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