Methyl iodide → HCID 54456549, compound

HRID 1585809Notes

Reaction equation

HRID 1585809 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([CH3:21])[C:13](=[O:14])[N:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11](=[O:20])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH3:24]I>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C@@:9]2([CH3:21])[C:13](=[O:14])[N:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11](=[O:20])[N:10]2[CH3:24])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15817571HCID 15817571, compound

Product 1

HCID 54456549HCID 54456549, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g of methyl (S)-(4-(4-cyanophenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetate (10.4 mmol) were dissolved in 15 ml of anhydrous dimethylformamide under argon. 11.4 mmol of sodium hydride in the form of a dispersion in mineral oil were added in an argon countercurrent. The reaction mixture was stirred at room temperature for 15 minutes. It was then treated with 721 μl of methyl iodide (11.4 mmol). The mixture was stirred at room temperature for 4 hours and then allowed to stand at room temperature overnight. The solution was concentrated. For purification, the substance was chromatographed on silica gel using methylene chloride/ethyl acetate (9.5:0.5). The fractions containing the pure substance were concentrated.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. waitto stand at room temperature overnight
  3. concentrationThe solution was concentrated
  4. customFor purification
  5. customthe substance was chromatographed on silica gel
  6. additionThe fractions containing the pure substance
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-cfdf688377ae47edb9250caf95c1386e
Source dataset
uspto-grants-1999_08
Patent number
US05939556

Reaction notes

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