Sodium Iodide → HCID 15923040, compound

HRID 443026Notes

Reaction equation

HRID 443026 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])(=O)=O>CN(C)C=O>[CH3:15][O:14][CH:3]([O:2][CH3:1])[C:4]1[CH:9]=[C:8]([O:10][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 32847943-(Dimethoxymethyl)-4-nitrophenolHCID 131203023-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonate

Product 1

HCID 15923040HCID 15923040, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5-Hydroxy-2-nitrobenzaldehyde dimethyl acetal (3.0 g) is dissolved in dry dimethylformamide (50 ml), and thereto are added sodium iodide (3.15 g), potassium carbonate (1.93 g) and 3-(t-butoxycarbonylamino)propyl tosylate (6.95 g). The mixture is stirred at 50° C. for three hours, and cooled to room temperature. The mixture is extracted with ethyl acetate, and the extract is washed with a saturated aqueous sodium chloride solution, and dried over sodium sulfate. The resultant is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography to give the title compound (5.22 g) as a pale yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe extract is washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationThe resultant is concentrated under reduced pressure
  6. customto remove the solvent
  7. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c4603cbeb62a498fbd042bb3ecbdb57c
Source dataset
uspto-grants-1999_04
Patent number
US05892043

Reaction notes

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