Butyl iodide → HCID 19735583, compound

HRID 326569Notes

Reaction equation

HRID 326569 reaction equation
[NH:1]1[C:9]2[C:8](=[O:10])[N:7]3[CH2:11][CH2:12][CH2:13][CH2:14][C:6]3=[N:5][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[CH2:18]([N:1]1[C:9]2[C:8](=[O:10])[N:7]3[CH2:11][CH2:12][CH2:13][CH2:14][C:6]3=[N:5][C:4]=2[N:3]=[CH:2]1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 19735579HCID 19735579, compound

Product 1

HCID 19735583HCID 19735583, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 1.20 g (6.32 mmol) of Compound 24 obtained in Example 24 was suspended in 20 ml of dimethylformamide, 0.265 g (6.63 mmol) of 60% sodium hydride was added to the suspension at 0° C. After 30 minutes, 0.755 ml (6.63 mmol) of iodobutane was added and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent; chloroform:methanol=40:1) to afford 1.10 g (70.8%) of Compound 26 as white crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluting solvent; chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-8ec4bd847ea945e78e688cc363a6167e
Source dataset
uspto-grants-1993_12
Patent number
US05270316

Reaction notes

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