Water → HCID 22401676, compound

HRID 260514Notes

Reaction equation

HRID 260514 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)[CH2:17][CH2:18][CH3:19].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)[CH2:17][CH2:18][CH3:19].[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)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 15337421HCID 15337421, compound

Product 2

HCID 22401676HCID 22401676, compoundYield 71%HCID 22401702HCID 22401702, compoundYield 26%

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 2.20 ml (19.3 mmol) of butyl iodide were added to the solution, followed by stirring at room temperature for one hour. 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 2.30 g (71%) of Compound 32 and 0.84 g (26%) of Compound 33, 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-d264f6e56df74406b2b8dc2d1593f674
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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