Water → HCID 22401667, compound

HRID 260512Notes

Reaction equation

HRID 260512 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][CH3:18].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][CH3:18].[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][CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 15337421HCID 15337421, compound

Product 2

HCID 22401667HCID 22401667, compoundYield 64%HCID 22401672HCID 22401672, compoundYield 25%

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 0.93 g (23.3 mmol) of sodium hydride. (60%) and 3.77 ml (38.6 mmol) of propyl 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 1.95 g (64%) of Compound 28 and 0.75 g (25%) of Compound 29, respectively. Each compound was recrystallized from ethanol for purification.

Workup

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

Sources & evidence

ORD record
ord-32518b94c4d24ce69bb9b1c8023d944f
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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