Iodoethane → HCID 12051977, compound

HRID 1871933Notes

Reaction equation

HRID 1871933 reaction equation
[CH2:1]([CH:4]([N:8]1[C:12]2[N:13]=[C:14]([CH3:27])[N:15]=[C:16]([NH:17][C:18]3[C:19]([CH3:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=3[CH3:24])[C:11]=2[N:10]=[N:9]1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[H-].[Na+].[CH2:30](I)[CH3:31]>CN(C)C=O.O>[CH2:30]([N:17]([C:18]1[C:19]([CH3:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=1[CH3:24])[C:16]1[C:11]2[N:10]=[N:9][N:8]([CH:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[C:12]=2[N:13]=[C:14]([CH3:27])[N:15]=1)[CH3:31]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12051976HCID 12051976, compound

Product 1

HCID 12051977HCID 12051977, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 47, Part B (400 mg, 1.09 mmol) was treated with sodium hydride (40 mg, 1.31 mmol, 80%) and ethyl iodide (0.130 ml, 1.63 mmol) in dry dimethylformamide (10 ml) and stirred at room temperature for 15 hours. The reaction was diluted with 150 ml water, and extracted with 3×30 ml ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to dryness. Chromatography on silica gel (20 g, 1/3 hexanes/ethyl acetate) afforded the desired product, 373 mg (87%) as a clear viscous oil.

Workup

  1. extractionextracted with 3×30 ml ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-c5d18d33571549908c6578b53ebfd9c8
Source dataset
uspto-grants-2000_08
Patent number
US06107300

Reaction notes

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