Iodoethane → HCID 18427734, compound

HRID 1871931Notes

Reaction equation

HRID 1871931 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]2[N:10]=[C:11]([CH3:24])[N:12]=[C:13]([NH:14][C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:8]=2[N:7]=[N:6]1.[H-].[Na+].[CH2:27](I)[CH3:28]>CN(C)C=O.O>[CH2:27]([N:14]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])[C:13]1[C:8]2[N:7]=[N:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:9]=2[N:10]=[C:11]([CH3:24])[N:12]=1)[CH3:28]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18427769HCID 18427769, compound

Product 1

HCID 18427734HCID 18427734, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 38, Part B (150 mg, 0.46 mmol) was treated with sodium hydride (17 mg, 0.55 mmol, 80%) and ethyl iodide (55 ml, 0.69 mmol) in dry dimethylformamide (3 ml) and stirred at room temperature for 48 h. The reaction was diluted with 50 ml water, and extracted with 4-30 ml methylene chloride. The combined organic extracts were dried over anydrous magnesium sulfate, filtered, and concentrated in vacuo to dryness. Chromatography on silica gel (50 g, 1/1 hexanes/ethyl acetate) afforded the desired product, 144 mg (88%) as a clear viscous oil. CI-HRMS calcd. for C19H27N6O1 (M+H): 355.2246. Found: 355.2240.

Workup

  1. extractionextracted with 4-30 ml methylene chloride
  2. dry with materialThe combined organic extracts were dried over anydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-b6a831b29124439096855efe8e52d974
Source dataset
uspto-grants-2000_08
Patent number
US06107300

Reaction notes

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