Water → HCID 22401693, compound

HRID 260513Notes

Reaction equation

HRID 260513 reaction equation
[NH:1]1[C:5]2[N:6]=[C:7]3[S:13][CH2:12][CH2:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=[N:2]1.[H-].[Na+].[CH:16](I)([CH3:18])[CH3:17].O>CN(C)C=O>[CH:16]([N:1]1[C:5]2[N:6]=[C:7]3[S:13][CH2:12][CH2:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=[N:2]1)([CH3:18])[CH3:17].[CH:16]([N:2]1[CH:3]=[C:4]2[C:5]([N:6]=[C:7]3[S:13][CH2:12][CH2:11][N:8]3[C:9]2=[O:10])=[N:1]1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 15337421HCID 15337421, compound

Product 2

HCID 22401681HCID 22401681, compoundYield 29%HCID 22401693HCID 22401693, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 50 ml of dimethylformamide was dissolved 2.50 g (12.9 mmol) of Compound 1 prepared in Example 1, and 0.77 g (19.3 mmol) of sodium hydride (60%) and 1.92 ml (19.3 mmol) of isopropyl iodide were added to the solution, followed by stirring at room temperature for 2 hours. After addition of water and evaporation of the solvent, the residue was subjected to partition between chloroform and water, and the chloroform layer was concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (100:1). The first and second main fractions gave 1.89 g (62%) of Compound 30 and 8.88 g (29%) of Compound 31, respectively. Each compound was recrystallized from ethanol for purification.

Workup

  1. additionwere added to the solution
  2. customto partition between chloroform and water
  3. concentrationthe chloroform layer was concentrated to dryness under reduced pressure
  4. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-001e0eec388d45c499e6c2fe7a6f830a
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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