Methyl iodide → HCID 69849154, compound

HRID 1459398Notes

Reaction equation

HRID 1459398 reaction equation
[C:1]12([N:11]3[C:15](=[O:16])[C:14]([CH2:23][C:24]4[CH:28]=[CH:27][O:26][CH:25]=4)([CH2:17][C:18]4[CH:22]=[CH:21][O:20][CH:19]=4)[NH:13][C:12]3=[O:29])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH3:32]I>C1COCC1>[C:1]12([N:11]3[C:15](=[O:16])[C:14]([CH2:23][C:24]4[CH:28]=[CH:27][O:26][CH:25]=4)([CH2:17][C:18]4[CH:22]=[CH:21][O:20][CH:19]=4)[N:13]([CH3:32])[C:12]3=[O:29])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69849045HCID 69849045, compound

Product 1

HCID 69849154HCID 69849154, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a N2 atmosphere was combined 3-adamantan-1-yl 5,5-bis-furan-3-ylmethyl-imidazolidine-2,4-dione (0.100 g, 0.25 mmol) in 2 ml of dry THF. To this solution was added a 60% dispersion of sodium hydride (11.1 mg, 0.28 mmol) and the suspension was allowed to stir for 1.5 hours. To this reaction mixture was then added methyl iodide (32 μl, 0.508 mmol) and the reaction mixture was allowed to stir for 30 minutes and quenched with water and extracted with 2×30 ml of methylene chloride (CH2Cl2). The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo to yield 0.103 g of the title compound.

Workup

  1. stirringto stir for 30 minutes
  2. customquenched with water
  3. extractionextracted with 2×30 ml of methylene chloride (CH2Cl2)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5167b5240444d9ba588c882a53c4df6
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

Loading…