Iodoethane → HCID 12051975, compound

HRID 1871932Notes

Reaction equation

HRID 1871932 reaction equation
[CH2:1]([CH:3]([N:7]1[C:11]2[N:12]=[C:13]([CH3:26])[N:14]=[C:15]([NH:16][C:17]3[C:18]([CH3:25])=[N:19][C:20]([CH3:24])=[CH:21][C:22]=3[CH3:23])[C:10]=2[N:9]=[N:8]1)[CH2:4][CH2:5][CH3:6])[CH3:2].[H-].[Na+].[CH2:29](I)[CH3:30]>CN(C)C=O.O>[CH2:29]([N:16]([C:17]1[C:18]([CH3:25])=[N:19][C:20]([CH3:24])=[CH:21][C:22]=1[CH3:23])[C:15]1[C:10]2[N:9]=[N:8][N:7]([CH:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH3:6])[C:11]=2[N:12]=[C:13]([CH3:26])[N:14]=1)[CH3:30]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12051974HCID 12051974, compound

Product 1

HCID 12051975HCID 12051975, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 45, Part B (250 mg, 0.71 mmol) was treated with sodium hydride (26 mg, 0.85 mmol, 80%) and ethyl iodide (0.85 ml, 1.07 mmol) in dry dimethylformamide (7 ml) and stirred at room temperature for 15 h. 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, 221 mg (81%) 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-961ff47673d746a8b09564212ea806e7
Source dataset
uspto-grants-2000_08
Patent number
US06107300

Reaction notes

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