Water → HCID 22401687, compound

HRID 260511Notes

Reaction equation

HRID 260511 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+].[CH2:16](I)[CH3:17].O>CN(C)C=O>[CH2:16]([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)[CH3:17].[CH2:16]([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)[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 15337421HCID 15337421, compound

Product 2

HCID 22401686HCID 22401686, compoundYield 22%HCID 22401687HCID 22401687, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 40 ml of dimethylformamide was dissolved 2.07 g (10.7 mmol) of Compound 1 prepared in Example 1, and 0.77 g (19.3 mmol) of sodium hydride (60%) and 2.56 ml (32.0 mmol) of ethyl iodide were added to the solution, followed by stirring at room temperature for 6 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 1.24 g (53%) of Compound 26 and 0.51 g (22%) of Compound 27, respectively. Compound 26 and Compound 27 were recrystallized from dimethylformamide/water and ethanol, respectively, 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-821b3ddf37e4481eb1522bc593ceeadd
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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