Methyl iodide → HCID 6373052, compound

HRID 1458548Notes

Reaction equation

HRID 1458548 reaction equation
[C:1]([N:4]1[CH2:9][C:8](=[O:10])[NH:7]/[C:6](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)/[C:5]1=[O:20])(=[O:3])[CH3:2].CI.[C:23](=O)([O-])[O-].[Na+].[Na+].[C:29]([O:32][CH2:33][CH3:34])(=O)C>CN(C=O)C>[C:1]([N:4]1[CH2:9][C:8](=[O:10])[N:7]([CH3:23])/[C:6](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)/[C:5]1=[O:20])(=[O:3])[CH3:2].[C:1]([N:4]1[CH2:34][C:33]([O:32][CH3:29])=[N:7][C:6](=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:5]1=[O:20])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 5392210HCID 5392210, compound

Product 2

HCID 6373052HCID 6373052, compoundYield 66%HCID 54000698HCID 54000698, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3Z)-1-Acetyl-3-(4-methoxybenzylidene)-2,5-piperazinedione (9) (2.0 g, 7.3 mmol), methyl iodide (0.46 ml, 7.3 mmol), and sodium carbonate (800 mg, 7.5 mmol) in dry DMF (50 ml) was stirred under an atmosphere of dry nitrogen for 3 days. The reaction mixture was then poured into ethyl acetate (500 ml) and washed with water (4×100 ml) and brine. The organic phase was separated, dried (MgSO4), and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, EtOAc:Hexane, 1:1) to give (3Z)-1-acetyl-3-(4-methoxybenzylidene)-4-methyl-2,5-piperazinedione (10) 1.38 g (66%) as a yellow solid and 1-acetyl-5-methoxy-3-(4-methoxybenzylidene)-3,6-dihydropyrazin-2-one (11) 248 mg (11.8%) as a bright yellow solid.

Workup

  1. washwashed with water (4×100 ml) and brine
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography (silica, EtOAc:Hexane, 1:1)

Sources & evidence

ORD record
ord-e462ed109e5d4f98a42374bb6576aad9
Source dataset
uspto-grants-1998_12
Patent number
US05852018

Reaction notes

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