Sodium hydride → HCID 69686096, compound

HRID 1058938Notes

Reaction equation

HRID 1058938 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]1[NH:9][C:8](=[O:10])[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]1=[O:14])[CH3:3].[H-].[Na+].[H][H].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>CN(C)C=O>[CH3:3][N:2]([CH:4]=[C:5]1[N:9]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[C:8](=[O:10])[N:7]([CH:11]([CH3:12])[CH3:13])[C:6]1=[O:14])[CH3:1]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 69686670HCID 69686670, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69686096HCID 69686096, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg of 5-dimethylaminomethylene-3-isopropylimidazolidine-2,4-dione in 2 ml of dimethylformamide was added 425 mg of sodium hydride (as a 60% dispersion in mineral oil). The mixture was stirred until evolution of hydrogen gas had ceased. The solution was then treated with 1.5 ml of 4-methoxybenzyl chloride and stirring continued overnight at rt. The mixture was partitioned between ethyl acetate and water and the organic layer dried, filtered and concentrated. The residue was purified by flash chromatography eluting with 1:1 ethyl acetate: haxane to give 85 mg of a colourless oil. 1H NMR (400 MHz, deuteriochloroform): δ=1.40 (6H, d, J=7 Hz), 3.02 (6H, s), 3.72 (3H, s), 4.38 (1H, septet, J=7 Hz), 4.60 (2H, s), 5.96 (1H, s), 6.80 (2H, d, J=8 Hz), 7.05 (2H, d, J=8 Hz).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe organic layer dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-2458c6309db7432a8769ea64bcd5ef36
Source dataset
uspto-grants-2003_02
Patent number
US06518293B2

Reaction notes

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