Acetic Acid → HCID 19753281, compound

HRID 483638Notes

Reaction equation

HRID 483638 reaction equation
[H-].[Na+].[CH3:3][CH:4]([N:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12])[C:5]#[CH:6].CI.[C:15](O)(=O)C>C1COCC1.CO>[CH3:15][N:9]1[CH2:10][CH2:11][N:7]([CH:4]([CH3:3])[C:5]#[CH:6])[C:8]1=[O:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15669658HCID 15669658, compound

Product 1

HCID 19753281HCID 19753281, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.2 g of 50% in oil) was added at 0° C. to a stirred solution of 1-(1-methyl-2-propynyl)-2-imidazolidinone (2.1 g) in dry THF (50 mL). After 15 min methyl iodide (3.0 mL) was added and the solution was stirred for an additional 30 min. Acetic acid (0.6 mL) and methanol (3 mL) were added and the solvent was removed under reduced pressure and the residual oil was partitioned between ethyl acetate and sodium hydroxide (10 mL of 2N). The ethyl acetate was removed and the crude product was chromatographed on silica gel to give 2.5 g of 1-methyl-3-(1-methyl-2-propynyl)-2-imidazolidinone as an oil.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residual oil was partitioned between ethyl acetate and sodium hydroxide (10 mL of 2N)
  3. customThe ethyl acetate was removed
  4. customthe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-679c1e87e4db472fa604b14941ae4c52
Source dataset
uspto-grants-1993_07
Patent number
US05225567

Reaction notes

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